Water → HCID 18477102, compound

HRID 2188208Notes

Reaction equation

HRID 2188208 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1.Cl.[CH2:18]([CH2:25][NH:26][CH2:27][CH:28]1[CH2:37][CH2:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]1=[O:38])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CCCCCC.C(OCC)C>[CH2:18]([CH2:25][NH:26][CH2:27][CH:28]1[CH2:37][CH2:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]1([C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)[OH:38])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 962WaterHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 18477078HCID 18477078, compoundHCID 178418339Butyllithium

Product 1

HCID 18477102HCID 18477102, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a cooled (−78° C.), stirred mixture of n-butyllithium in hexane (1.6 M, 34.7 cm3) and diethyl ether (25 cm3) was added 4-bromobenzotrifluoride (7.8 g). After a further 15 min, 2-(N-benzylmethylamino)methyl-3,4-dihydro-2H-naphthalen-1-one hydrochloride (prepared using methods described in Process 1) was added portion-wise. The reaction mixture was then stirred for 1 h before being allowed to warm to room temperature and then water (50 cm3) was added. The organic layer was separated and washed with water (50 cm3). It was then extracted with hydrochloric acid (2 M, 50 cm3) and the acidic aqueous portion was basified with solid sodium carbonate and extracted with dichloromethane (100 cm3). The combined organic extracts were dried (Na2SO4) and the solvent was removed under reduced pressure to afford the title compound as a colourless oil.

Workup

  1. stirringThe reaction mixture was then stirred for 1 h
  2. temperatureto warm to room temperature
  3. customThe organic layer was separated
  4. washwashed with water (50 cm3)
  5. extractionIt was then extracted with hydrochloric acid (2 M, 50 cm3)
  6. extractionextracted with dichloromethane (100 cm3)
  7. dry with materialThe combined organic extracts were dried (Na2SO4)
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-32f412b3ea864102a4ef83e0909d90d0
Source dataset
uspto-grants-2002_06
Patent number
US06410592B1

Reaction notes

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