1-butylpiperidin-4-amine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 4.69 Grams of 4-amino-1-n-butylpiperidine in 100 milliliters of chloroform were added to a suspension of 5.79 grams of 4-nitrophthalic anhydride in 75 milliliters of chloroform and the solution was evaporated to dryness. 40 Milliliters of acetic anhydride were added and the mixture was then heated on a steam bath for half an hour. The excess acetic anhydride was evaporated off and the residue dissolved in 40 milliliters of methanol and ethereal hydrogen chloride was added to give a solid which was collected giving 2.50 grams of the title compound as the monohydrochloride. the solution was evaporated to dryness 40 Milliliters of acetic anhydride were added the mixture was then heated on a steam bath for half an hour The excess acetic anhydride was evaporated off the residue dissolved in 40 milliliters of methanol ethereal hydrogen chloride was added to give a solid which was collected

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

Procedure: 4-Amino-1-n-butylpiperidine and 3,6-dichlorophthalic anhydride are reacted in a similar manner to that described in Example 3 to give the title compound.

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

Procedure: 4-Amino-1-n-butylpiperidine and 3,6-dichlorophthalic anhydride are reacted in a similar manner to that described in Example 3 to give the title compound.

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

Procedure: 2-(7-Chloro-4-quinolylamino)-3-methyl benzoic acid is converted to the acid chloride which is reacted with 4-amino-1-n-butyl piperidine as in Example 1 to give the title compound.

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: N-(1-Butyl-4-piperidinyl)-8-methoxy-4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]carbonyl]phenyl]amino]-3-quinolinecarboxamide was prepared as a hygroscopic material (0.215 hydrate) by coupling 8-methoxy-4-[[4-[[[1-(phenylmethyl)-4-piperidinyl]amino]carbonyl]phenyl]amino]-3-quinolinecarboxylic acid and 4-amino-1-butylpiperidine as described for Example 17, Step 5. 4-Amino -1-butyl-piperidine can be prepared from 4-bromobutane and 1,4-dioxa-8-azaspiro[4.5]-decane as described in U.S. Pat. Nos. 3,875,165 and 4,816,464: mp 215°-220 ° C.; 1H NMR (Me2SO-d6, 400 MHz) δ 9.50 (s, 1 H), 8.77 (s, 1 H), 8.39 (d, J=7.5 Hz, 1 H), 8.01 (d, J=7.8 Hz, 1 H), 7.70 (d, J=8.6 Hz, 2 H), 7.57 (d, J= 8.4 Hz, 1 H), 7.41 (m, 1 H), 7.18-7.32 (m, 6 H), 6.88 (d, J=8.6 Hz, 2 H), 3.95 (s, 3 H), 3.72-3.76 (m, 1 H), 3.44-3.49 (m, 3 H), 2.68-2.80 (m, 4 H), 2.14-2.19 (m, 2 H), 1.95-2.01 (m, 2 H), 1.71-1.83 (m, 4 H), 1.53-1.60 (m, 4 H), 1,1-1.4 (m, 6 H), 0.8 (t, J=7.24 Hz, 3 H); Karl Fischer, 0.58% H2O.

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

Procedure: 4-(2-Chloro-4-quinolylamino)-2-chlorobenzene sulphonic acid is converted to the corresponding sulphonylchloride hydrochloride and reacted with 4-amino-1-butylpiperidine in a similar manner to that described in Example 1(b) to give the title compound.