heptan-3-amine

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2 (1 mmol), 3-aminoheptane (1.2 mmol), Pd2(DBA)3 (0.02 mol, 4 mol % Pd, 18 mg), BINP (0.04 mmol, 25 mg), NaOtBu (1.4 mmol, 134 mg), and toluene (0.11 M with 3-bromopyridine, 9 ml) is heated to 70° C. under nitrogen until 2 is consumed. The reaction is then cooled to room temperature, and taken up in 10 ml diethyl ether, washed 3 times with 10 ml saturated brine, dried over MgSO4, and condensed in vacuo . The crude product is purified by flash chromatography to afford 3. is consumed The reaction is then cooled to room temperature washed 3 times with 10 ml saturated brine dried over MgSO4, and condensed in vacuo The crude product is purified by flash chromatography to afford 3

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2 (1 mmol), 3-aminoheptane (1.2 mmol), Pd2(DBA)3 (0.02 mol, 4 mol % Pd, 18 mg), BINP (0.04 mmol, 25 mg), NaOtBu (1.4 mmol, 134 mg), and toluene (0.11 M with 3-bromopyridine, 9 ml) is heated to 70° C. under nitrogen until 2 is consumed. The reaction is then cooled to room temperature, and taken up in 10 ml diethyl ether, washed 3 times with 10 ml saturated brine, dried over MgSO4, and condensed in vacuo . The crude product is purified by flash chromatography to afford 3. is consumed The reaction is then cooled to room temperature washed 3 times with 10 ml saturated brine dried over MgSO4, and condensed in vacuo The crude product is purified by flash chromatography to afford 3

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2 (1 mmol), 3-aminoheptane (1.2 mmol), Pd2(DBA)3 (0.02 mmol, 4 mol % Pd, 18 mg), BINP (0.04 mmol, 25 mg), NaOtBu (1.4 mmol, 134 mg), and toluene (0.11 M with 3-bromopyridine, 9 ml) is heated to 70° C. under nitrogen until 2 is consumed. The reaction is then cooled to room temperature, and taken up in 10 ml diethyl ether, washed 3 times with 10 ml saturated brine, dried over MgSO4, and condensed in vacuo. The crude product is purified by flash chromatography to afford 3. is consumed The reaction is then cooled to room temperature washed 3 times with 10 ml saturated brine dried over MgSO4, and condensed in vacuo The crude product is purified by flash chromatography to afford 3

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2 (1 mmol), 3-aminoheptane (1.2 mmol), Pd2(DBA)3 (0.02 mmol, 4 mol % Pd, 18 mg), BINP (0.04 mmol, 25 mg), NaOtBu (1.4 mmol, 134 mg), and toluene (0.11 M with 3-bromopyridine, 9 ml) is heated to 70° C. under nitrogen until 2 is consumed. The reaction is then cooled to room temperature, and taken up in 10 ml diethyl ether, washed 3 times with 10 ml saturated brine, dried over MgSO4, and condensed in vacuo. The crude product is purified by flash chromatography to afford 3. is consumed The reaction is then cooled to room temperature washed 3 times with 10 ml saturated brine dried over MgSO4, and condensed in vacuo The crude product is purified by flash chromatography to afford 3

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2 (1 mmol), 3-aminoheptane (1.2 mmol), Pd2(DBA)3 (0.02 mol, 4 mol % Pd, 18 mg), BINP (0.04 mmol, 25 mg), NaOtBu (1.4 mmol, 134 mg), and toluene (0.11 M with 3-bromopyridine, 9 ml) is heated to 70° C. under nitrogen until 2 is consumed. The reaction is then cooled to room temperature, and taken up in 10 ml diethyl ether, washed 3 times with 10 ml saturated brine, dried over MgSO4, and condensed in vacuo . The crude product is purified by flash chromatography to afford 3. is consumed The reaction is then cooled to room temperature washed 3 times with 10 ml saturated brine dried over MgSO4, and condensed in vacuo The crude product is purified by flash chromatography to afford 3

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: If heptan-3-ol is reacted similarly with ammonia at 130° C., 80% of theory of di-3-heptylamine, 18.5% of theory of 3-heptylamine and 0.5% of theory of unconverted alcohol are obtained.

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2 (1 mmol), 3-aminoheptane (1.2 mmol), Pd2(DBA)3 (0.02 mmol, 4 mol % Pd, 18 mg), BINP (0.04 mmol, 25 mg), NaOtBu (1.4 mmol, 134 mg), and toluene (0.11 M with 3-bromopyridine, 9 ml) is heated to 70° C. under nitrogen until 2 is consumed. The reaction is then cooled to room temperature, and taken up in 10 ml diethyl ether, washed 3 times with 10 ml saturated brine, dried over MgSO4, and condensed in vacuo. The crude product is purified by flash chromatography to afford 3. is consumed The reaction is then cooled to room temperature washed 3 times with 10 ml saturated brine dried over MgSO4, and condensed in vacuo The crude product is purified by flash chromatography to afford 3

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2 (1 mmol), 3-aminoheptane (1.2 mmol), Pd2(DBA)3 (0.02 mol, 4 mol % Pd, 18 mg), BINP (0.04 mmol, 25 mg), NaOtBu (1.4 mmol, 134 mg), and toluene (0.11 M with 3-bromopyridine, 9 ml) is heated to 70° C. under nitrogen until 2 is consumed. The reaction is then cooled to room temperature, and taken up in 10 ml diethyl ether, washed 3 times with 10 ml saturated brine, dried over MgSO4, and condensed in vacuo . The crude product is purified by flash chromatography to afford 3. is consumed The reaction is then cooled to room temperature washed 3 times with 10 ml saturated brine dried over MgSO4, and condensed in vacuo The crude product is purified by flash chromatography to afford 3