Sodium Hydroxide → 6-Benzyloxy-2-dimethylaminobenzo[b]thiophen-3-yl 3-Methoxy-4-[(1-pyrrolidinyl)methyl]phenyl Ketone

HRID 1387091

Reaction equation

HRID 1387091 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH:16]=[C:15]([N:17]([CH3:19])[CH3:18])[S:14][C:13]=2[CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=1[CH2:32][N:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1)[C:26](Cl)=[O:27].[OH-].[Na+]>ClC1C=CC=CC=1.[Cl-].[Na+].O>[CH3:21][O:22][C:23]1[CH:24]=[C:25]([C:26]([C:16]2[C:12]3[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:20][C:13]=3[S:14][C:15]=2[N:17]([CH3:18])[CH3:19])=[O:27])[CH:29]=[CH:30][C:31]=1[CH2:32][N:33]1[CH2:34][CH2:35][CH2:36][CH2:37]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 106129946-Benzyloxy-2-dimethylaminobenzo[b]thiopheneHCID 217063533-Methoxy-4-[(1-pyrrolidinyl)methyl]benzoyl chloride

Product 1

HCID 106730126-Benzyloxy-2-dimethylaminobenzo[b]thiophen-3-yl 3-Methoxy-4-[(1-pyrrolidinyl)methyl]phenyl KetoneYield 84%

Reagents, catalysts & solvents 2

HCID 7964ChlorobenzeneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 6-benzyloxy-2-(dimethylamino)benzo[b]thiophene (2.5 g, 8.8 mmol) and 3-methoxy-4-[(1-pyrrolidinyl)methyl]benzoyl chloride (3.0 g, 1.3 equiv) in chlorobenzene (30 mL) was heated at 135° C. under nitrogen for 2 h. The cooled reaction mixture was diluted with brine (100 mL), neutralized with NaOH solution (5.0 M), and extracted with dichloromethane (100 mL×3). The combined organic layers were dried with sodium sulfate and concentrated under reduced pressure. Chromatography with Et3N:EtOAc (5:95) afforded the product as a brown oil (3.7 g, 84%).

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with dichloromethane (100 mL×3)
  3. dry with materialThe combined organic layers were dried with sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5e96b6e0ef1b4c77ae2c29d8b72c03eb
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Linked notes

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