Methanol → (+/-)-4-(alpha-(trans-2,5-dimethyl-1-piperazinyl)-5-(tert-butyldimethylsilyloxy)-2-fluorobenzyl)-N,N-diethylbenzamide

HRID 2258329Notes

Reaction equation

HRID 2258329 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([F:30])=[C:13]([CH:29]=1)[CH:14]([C:16]1[CH:28]=[CH:27][C:19]([C:20]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=1)O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].S(Cl)(Cl)=O.[CH3:35][C@H:36]1[CH2:41][NH:40][C@H:39]([CH3:42])[CH2:38][NH:37]1.CO>ClCCl>[CH3:35][C@H:36]1[CH2:41][NH:40][C@H:39]([CH3:42])[CH2:38][N:37]1[CH:14]([C:16]1[CH:28]=[CH:27][C:19]([C:20]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=1)[C:13]1[CH:29]=[C:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH:10]=[CH:11][C:12]=1[F:30]

Participants

6

Reactant 4

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2206722,5-Dimethylpiperazine, trans-HCID 541141914-(5-(tert-butyldimethylsilyloxy)-2-fluoro-alpha-hydroxybenzyl)-N,N-diethylbenzamide

Product 1

HCID 69941891(+/-)-4-(alpha-(trans-2,5-dimethyl-1-piperazinyl)-5-(tert-butyldimethylsilyloxy)-2-fluorobenzyl)-N,N-diethylbenzamideYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The benzhydrol from above (1.77 g, 4.1 mmol) was treated with thionyl chloride (0.45 mL, 6.2 mmol) by the method in Example 1. The crude product (approximately 4.1 mmol) was treated with trans-2,5-dimethylpiperazine (1.64 g, 14.3 mmol) as in Example 1. Chromatography on silica gel with 1-7% methanol in dichloromethane gave 0.44 g (20% from benzhydryl chloride) of (±)-4-(α-(trans-2,5-dimethyl-1-piperazinyl)-5-(tert -butyldimethylsilyloxy)-2-fluorobenzyl)-N,N-diethylbenzamide as a yellow oil.

Sources & evidence

ORD record
ord-97d569e7719f40dbafe718ff30cf782b
Source dataset
uspto-grants-1997_08
Patent number
US05658908

Reaction notes

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