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

HRID 1460095Notes

Reaction equation

HRID 1460095 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 9, 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-879a55920b124dbf9bd2aa7897296a47
Source dataset
uspto-grants-1998_12
Patent number
US05854249

Reaction notes

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