Reaction #4082672
Related Literature (1)
openreactiondata ↗doi:10.1039/C8SC04228D
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-9710297f66b64d0aa7a9fd38589ba0eaNo renderable structure data available
CC1(CNCCC1N)CChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 3,3-dimethylpiperidin-4-amine |
|---|---|
| IUPAC Name | — |
| CAS Number | 396133-38-3 |
| Database ID | 10214389 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
3,3-dimethylpiperidin-4-amine (CAS 396133-38-3) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 10214389
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
11 reactions · 11 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-9710297f66b64d0aa7a9fd38589ba0eaConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 20% Pd(OH)2 on carbon (0.3 g) and 4-amino-1-benzyl-3,3-dimethylpiperidine (1.6 g, 7.33 mmol) in methanol (25 ml) was stirred in hydrogen atmosphere (1 atm.) at 30° C. for 6 hr. The catalyst was filtered off, washed with methanol and filtrate was concentrated to dryness to afford 4-amino-3,3-dimethylpiperidine. Yield 0.7 g (75%), C7H16N2, m/z 129 (M+1), PMR (CDCl3): 0.9 (s, 6H), 1.5 (m, 2H), 1.58 (bs, 2H, D2O exchangeable), 2.26-2.68 (m, 4H), 3.06 (m, 1H), 3.52 (bs, 1H, D2O exchangeable). The catalyst was filtered off washed with methanol and filtrate was concentrated to dryness
Source ID: ord-a35043372c134177b158e7339a6f229bConditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 10% palladium on carbon (7.5 g) and (−)-4-amino-1-benzyloxycarbonyl-3,3-dimethylpiperidine (cf. Preparation 19, Step 4, 50 g, 191.0 mmol) in methanol (500 ml) was stirred under hydrogen atmosphere (30 atm.) at 30° C. for 6 hr. The catalyst was filtered off, washed with 100 ml methanol and filtrate was concentrated to dryness to afford (−)-4-amino-3,3-dimethylpiperidine, which was further purified by vacuum distillation to give 16.8 (71%) titled compound. The catalyst was filtered off washed with 100 ml methanol and filtrate was concentrated to dryness
Source ID: ord-e88962d282254613aeb5ddfcf747caeeConditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 10% palladium on carbon (7.5 g) and (−)-4-amino-1-benzyloxycarbonyl-3,3-dimethylpiperidine (cf. Preparation 19, Step 4, 50 g, 191.0 mmol) in methanol (500 ml) was stirred under hydrogen atmosphere (30 atm.) at 30° C. for 6 hr. The catalyst was filtered off, washed with 100 ml methanol and filtrate was concentrated to dryness to afford (−)-4-amino-3,3-dimethylpiperidine, which was further purified by vacuum distillation to give 16.8 (71%) titled compound. The catalyst was filtered off washed with 100 ml methanol and filtrate was concentrated to dryness
Source ID: ord-e88962d282254613aeb5ddfcf747caeeConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 20% Pd(OH)2 on carbon (0.3 g) and 4-amino-1-benzyl-3,3-dimethylpiperidine (1.6 g, 7.33 mmol) in methanol (25 ml) was stirred in hydrogen atmosphere (1 atm.) at 30° C. for 6 hr. The catalyst was filtered off, washed with methanol and filtrate was concentrated to dryness to afford 4-amino-3,3-dimethylpiperidine. Yield 0.7 g (75%), C7H16N2, m/z 129 (M+1), PMR (CDCl3): 0.9 (s, 6H), 1.5 (m, 2H), 1.58 (bs, 2H, D2O exchangeable), 2.26-2.68 (m, 4H), 3.06 (m, 1H), 3.52 (bs, 1H, D2O exchangeable). The catalyst was filtered off washed with methanol and filtrate was concentrated to dryness
Source ID: ord-a2f19aa3cba3489899d272dd1e24dcb8Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-9710297f66b64d0aa7a9fd38589ba0eaConditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 10% palladium on carbon (7.5 g) and (−)-4-amino-1-benzyloxycarbonyl-3,3-dimethylpiperidine (cf. Preparation 19, Step 4, 50 g, 191.0 mmol) in methanol (500 ml) was stirred under hydrogen atmosphere (30 atm.) at 30° C. for 6 hr. The catalyst was filtered off, washed with 100 ml methanol and filtrate was concentrated to dryness to afford (−)-4-amino-3,3-dimethylpiperidine, which was further purified by vacuum distillation to give 16.8 (71%) titled compound. The catalyst was filtered off washed with 100 ml methanol and filtrate was concentrated to dryness
Source ID: ord-1c467935bd2942d2a5b633810c1ab98bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 20% Pd(OH)2 on carbon (0.3 g) and 4-amino-1-benzyl-3,3-dimethylpiperidine (1.6 g, 7.33 mmol) in methanol (25 ml) was stirred in hydrogen atmosphere (1 atm.) at 30° C. for 6 hr. The catalyst was filtered off, washed with methanol and filtrate was concentrated to dryness to afford 4-amino-3,3-dimethylpiperidine. Yield 0.7 g (75%), C7H16N2, m/z 129 (M+1), PMR (CDCl3): 0.9 (s, 6H), 1.5 (m, 2H), 1.58 (bs, 2H, D2O exchangeable), 2.26-2.68 (m, 4H), 3.06 (m, 1H), 3.52 (bs, 1H, D2O exchangeable). The catalyst was filtered off washed with methanol and filtrate was concentrated to dryness
Source ID: ord-4c42fb88354f43b699ef1ff80d078f2bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 20% Pd(OH)2 on carbon (0.3 g) and 4-amino-1-benzyl-3,3-dimethylpiperidine (1.6 g, 7.33 mmol) in methanol (25 ml) was stirred in hydrogen atmosphere (1 atm.) at 30° C. for 6 hr. The catalyst was filtered off, washed with methanol and filtrate was concentrated to dryness to afford 4-amino-3,3-dimethylpiperidine. Yield 0.7 g (75%), C7H16N2, m/z 129 (M+1), PMR (CDCl3): 0.9 (s, 6H), 1.5 (m, 2H), 1.58 (bs, 2H, D2O exchangeable), 2.26-2.68 (m, 4H), 3.06 (m, 1H), 3.52 (bs, 1H, D2O exchangeable). The catalyst was filtered off washed with methanol and filtrate was concentrated to dryness
Source ID: ord-a35043372c134177b158e7339a6f229bConditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 10% palladium on carbon (7.5 g) and (−)-4-amino-1-benzyloxycarbonyl-3,3-dimethylpiperidine (cf. Preparation 19, Step 4, 50 g, 191.0 mmol) in methanol (500 ml) was stirred under hydrogen atmosphere (30 atm.) at 30° C. for 6 hr. The catalyst was filtered off, washed with 100 ml methanol and filtrate was concentrated to dryness to afford (−)-4-amino-3,3-dimethylpiperidine, which was further purified by vacuum distillation to give 16.8 (71%) titled compound. The catalyst was filtered off washed with 100 ml methanol and filtrate was concentrated to dryness
Source ID: ord-e88962d282254613aeb5ddfcf747caeeConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 20% Pd(OH)2 on carbon (0.3 g) and 4-amino-1-benzyl-3,3-dimethylpiperidine (1.6 g, 7.33 mmol) in methanol (25 ml) was stirred in hydrogen atmosphere (1 atm.) at 30° C. for 6 hr. The catalyst was filtered off, washed with methanol and filtrate was concentrated to dryness to afford 4-amino-3,3-dimethylpiperidine. Yield 0.7 g (75%), C7H16N2, m/z 129 (M+1), PMR (CDCl3): 0.9 (s, 6H), 1.5 (m, 2H), 1.58 (bs, 2H, D2O exchangeable), 2.26-2.68 (m, 4H), 3.06 (m, 1H), 3.52 (bs, 1H, D2O exchangeable). The catalyst was filtered off washed with methanol and filtrate was concentrated to dryness
Source ID: ord-a2f19aa3cba3489899d272dd1e24dcb8PubChem References
These sources are listed in the compound's public database record.
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