Acetic Anhydride → HCID 86616387, compound

HRID 1432136Notes

Reaction equation

HRID 1432136 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]([N:15]3[CH2:21][CH:20]4[N:22]([CH3:23])[CH:17]([CH2:18][CH2:19]4)[CH2:16]3)=[O:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:24]([O:27][C:28](=[O:30])[CH3:29])(=[O:26])[CH3:25].[OH-:31].[Na+]>ClCCl>[C:28]([OH:27])(=[O:30])/[CH:29]=[CH:11]/[C:13]([OH:14])=[O:31].[CH3:23][N:22]1[CH:20]2[CH2:19][CH2:18][CH:17]1[CH2:16][N:15]([C:13]([C:11]1[O:12][C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:24](=[O:26])[CH3:25])=[CH:3][CH:4]=3)=[CH:9][CH:10]=1)=[O:14])[CH2:21]2

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 11681151HCID 11681151, compound

Product 1

HCID 86616387HCID 86616387, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of [5-(4-amino-phenyl)-furan-2-yl]-(8-methyl-3,8-diaza-bicyclo[3.2.1]oct-3-yl)-methanone (0.40, 1.28 mmol), acetic acid anhydride (197 mg, 1.93 mmol) and dichloromethane (5 ml) was stirred at room temperature for 5 hours. Aqueous sodium hydroxide (5 ml, 1M) was added and the mixture was extracted twice with dichloromethane (2×10 ml). Chromatography on silica gel with dichloromethane, 10% methanol and 1% aqueous ammonia as solvent gave the title compound. The corresponding salt was obtained by addition of a diethyl ether and methanol mixture (9:1) saturated with fumaric acid. Mp. 257-259° C. Yield 515 mg (86%).

Workup

  1. extractionthe mixture was extracted twice with dichloromethane (2×10 ml)

Sources & evidence

ORD record
ord-3c75729911d146c5b85fbff073678a68
Source dataset
uspto-grants-2009_11
Patent number
US07612074B2

Reaction notes

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