Benzoyl chloride → (+/-)5-(4-Benzoylamino-phenyl)-furan-2-carboxylic acid (1-aza-bicyclo[2.2.2]oct-3-yl)-amide hydrochloric acid salt

HRID 2108692Notes

Reaction equation

HRID 2108692 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([NH:9][C:10]([C:12]1[O:13][C:14]([C:17]3[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=3)=[CH:15][CH:16]=1)=[O:11])[CH2:2]2.[C:24]([Cl:32])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl>[ClH:32].[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[CH:3]([NH:9][C:10]([C:12]1[O:13][C:14]([C:17]3[CH:18]=[CH:19][C:20]([NH:23][C:24](=[O:31])[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:21][CH:22]=3)=[CH:15][CH:16]=1)=[O:11])[CH2:2]2

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 181804805-(4-Amino-phenyl)-furan-2-carboxylic acid (1-aza-bicyclo[2.2.2]oct-3-yl)-amide

Product 1

HCID 86614760(+/-)5-(4-Benzoylamino-phenyl)-furan-2-carboxylic acid (1-aza-bicyclo[2.2.2]oct-3-yl)-amide hydrochloric acid salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-(4-amino-phenyl)-furan-2-carboxylic acid(1-aza-bicyclo[2.2.2]oct-3-yl)-amide (0.155 g, 0.5 mmol), dichloromethane (25 ml) and benzoyl chloride (0.117 ml, 1.0 mmol) was stirred for 3 hours at room temperature. The crude mixture was filtered. The product was precipitated from the filtrate by adding diethyl ether (5 ml) as hydrochloric acid salt. Yield 56 mg (25%). M.p. 215° C.

Workup

  1. filtrationThe crude mixture was filtered
  2. customThe product was precipitated from the filtrate
  3. additionby adding diethyl ether (5 ml) as hydrochloric acid salt

Sources & evidence

ORD record
ord-32d07f11964141e18e06c0008be1dd91
Source dataset
uspto-grants-2009_04
Patent number
US07514450B2

Reaction notes

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