Water → HCID 22717055, compound

HRID 1374129Notes

Reaction equation

HRID 1374129 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C([Li])(C)(C)C.[Br:30][CH2:31][Si:32]([CH3:35])([CH3:34])Cl.O>C(OCC)C>[C:21]([O:20][C:18]([N:15]1[CH2:14][CH2:13][N:12]([C:4]2[CH:5]=[C:6]([C:8]([F:10])([F:9])[F:11])[CH:7]=[C:2]([Si:32]([CH2:31][Br:30])([CH3:35])[CH3:34])[CH:3]=2)[CH2:17][CH2:16]1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 85476Silane, (bromomethyl)chlorodimethyl-HCID 22717044HCID 22717044, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 22717055HCID 22717055, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-65 °C

Procedure

A solution of tert-butyl 4-[3-bromo-5-(trifluoromethyl)-phenyl]-1-piperazine carboxylate (75 g, 183 mmoles) in diethyl ether, previously dried on molecular sieves, (1000 ml) was cooled to −65° C. and a 1.7M solution of tert-butyl lithium (215.6 ml, 366 mmoles) was added. After 30 minutes stirring bromomethyl-dimethyl-chlorosilane (49.9 ml, 366 mmoles) was added dropwise. After 2 hours stirring at −65° C., the reaction mixture was left at room temperature overnight. Water (600 ml) was added and the organic layer was washed with water, dried on MgSO4, filtered and evaporated.

Workup

  1. additionwas added dropwise
  2. waitthe reaction mixture was left at room temperature overnight
  3. washthe organic layer was washed with water
  4. customdried on MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-d20b81c3bb2f4d4f96c361395a239792
Source dataset
uspto-grants-2007_01
Patent number
US07164018B2

Reaction notes

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