Acetic Anhydride → HCID 18960744, compound

HRID 1708319Notes

Reaction equation

HRID 1708319 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:38]=[CH:37][C:17]([C:18]([N:20]3[CH2:25][CH2:24][CH:23]([N:26]4[C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[CH2:30][CH2:29][C:27]4=[O:28])[CH2:22][CH2:21]3)=[O:19])=[CH:16][CH:15]=2)[CH2:4][CH2:3]1.[C:39](OC(=O)C)(=[O:41])[CH3:40].C(N(CC)CC)C.CNN1C=CC(NC)=CC1>ClCCl.O>[C:39]([NH:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:38]=[CH:37][C:17]([C:18]([N:20]3[CH2:21][CH2:22][CH:23]([N:26]4[C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[CH2:30][CH2:29][C:27]4=[O:28])[CH2:24][CH2:25]3)=[O:19])=[CH:16][CH:15]=2)[CH2:6][CH2:7]1)(=[O:41])[CH3:40]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 18960746HCID 18960746, compoundHCID 223379141,4-Dimethylaminopyridine

Product 1

HCID 18960744HCID 18960744, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1-[1-{4-[5-(4-Amino-1-piperidinyl)pentyloxy]benzoyl}-4-piperidinyl]-3,4-dihydrocarbostyril (0.6 g) and acetic anhydride (0.2 ml) are dissolved in dichloromethane (20 ml), and thereto are added triethylamine (0.56 ml) and 1,4-dimethylaminopyridine (20 mg), and the mixture is stirred at room temperature overnight. Water is added to the reaction mixture and the mixture is extracted with chloroform, dried over sodium carbonate, and purified by silica gel column chromatography (eluent; dichloromethane:methanol=20:1) to give 1-[1-{4-[5-(4-acetylamino-1-piperidinyl)pentyloxy]benzoyl}-4-piperidinyl]-3,4-dihydrocarbostyril (310 mg) as colorless oil.

Workup

  1. extractionthe mixture is extracted with chloroform
  2. dry with materialdried over sodium carbonate
  3. custompurified by silica gel column chromatography (eluent; dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-62bec7bf53c0456290cd5d9a2a0bbe5d
Source dataset
uspto-grants-1994_10
Patent number
US05356904

Reaction notes

Loading…