Acetic Anhydride → HCID 53961561, compound

HRID 362931Notes

Reaction equation

HRID 362931 reaction equation
C(N(CC)CC)C.C(O[C:12](=[O:14])[CH3:13])(=O)C.[CH2:15]([NH:22][C:23](=[O:54])[NH:24][C:25]1[CH:52]=[CH:51][C:50]([NH2:53])=[CH:49][C:26]=1[C:27]([NH:29][CH:30]1[CH2:35][CH2:34][N:33]([CH:36]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:32][CH2:31]1)=[O:28])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>ClCCl>[CH2:15]([NH:22][C:23](=[O:54])[NH:24][C:25]1[CH:52]=[CH:51][C:50]([NH:53][C:12](=[O:14])[CH3:13])=[CH:49][C:26]=1[C:27]([NH:29][CH:30]1[CH2:31][CH2:32][N:33]([CH:36]([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:34][CH2:35]1)=[O:28])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 54299070HCID 54299070, compound

Product 1

HCID 53961561HCID 53961561, compoundYield 807.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.098 ml, 0.65 mmol) and acetic anhydride (0.067 ml, 0.07 mmol) were added to a solution of the 2-(N'-n-heptylureido)-5-amino-N-(1-diphenylmethylpiperidin-4-yl)-benzamide (0.32 g, 0.59 mmol) in dichloromethane (3 ml) at room temperature. The mixture was stirred for 24 hours and then concentrated. The residue was purified by column chromatography on silica gel (50% ethyl acetate in cyclohexane) to give 2-(N'-n-heptylureido)-5acetylamino-N-(1-diphenylmethylpiperidin-4-yl)benzamide (0.33 g, 96.0%): mp 113°-115° C., 1H NMR (CDCl3)ppm: 0.86 (3H, t), 1.27 (8H, m), 1.49-1.69 (4H, m), 1.92-2.08 (4H, m), 2.17 (3H, s), 2.85 (2H, m), 3.22 (2H, q), 3.90 (1H, m), 4.28 (1H, s), 4.57 (1H, t), 6.40 (1H, d), 7.03 (1H, dd), 7.15-7.40 (11H, m), 8.06 (1H, d), 8.30 (1H, d), 10.10 (1H, s).

Workup

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

Sources & evidence

ORD record
ord-eb52a03837324abeae07a3efe238246b
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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