1-Heptanamine → HCID 53946422, compound

HRID 362925Notes

Reaction equation

HRID 362925 reaction equation
O([C:8]([NH:10][C:11]1[CH:34]=[CH:33][CH:32]=[CH:31][C:12]=1[C:13]([NH:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:23])[CH2:18][CH2:17]1)=[O:14])=[O:9])C1C=CC=CC=1.[CH2:35]([NH2:42])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>C1(C)C=CC=CC=1>[CH2:35]([NH:42][C:8](=[O:9])[NH:10][C:11]1[CH:34]=[CH:33][CH:32]=[CH:31][C:12]=1[C:13]([NH:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:23])[CH2:18][CH2:17]1)=[O:14])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

Participants

4

Reactant 2

HCID 81271-HeptanamineHCID 53852154HCID 53852154, compound

Product 1

HCID 53946422HCID 53946422, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-phenoxycarbonylamino-N-(1-phenoxylcarbonylpiperidin-4-yl)benzamide (1.6 g, 3.5 mmol) and n-heptylamine (0.45 g, 3.9 mmol) in toluene (20 ml) was refluxed for 4 hours and then concentrated. The residue was purified by column chromatography on silica gel (50% ethyl acetate in petroleum ether) to give 2-(N'-n-heptylureido)-N-(1-phenoxy carbonylpiperidin-4-yl)benzamide: yield 95.0%: mp 142°-144° C.; 1H NMR (CDCl3)ppm: 0.88 (3H, t) 1.28-1.33 (7H, m), 19-1.62 (4H, m), 2.05-2.17 (2H, m), 3.04-3.19 (2H, m), 3.25 (2H, q), 4.10-4.15 (1H, m), 4.24-4.40 (2H, m), 4.59 (1H, t), 6.35 (1H, d), 6.92 (1H, t), 6.97-7.44 (8H, m), 8.40 (1H,d), 10.20 (1H, s).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by column chromatography on silica gel (50% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-0c4ad84f1a194235b310a9654cfd65f4
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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