Water → HCID 22038239, compound

HRID 1790485Notes

Reaction equation

HRID 1790485 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:30])[CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([O:28][CH3:29])[CH:26]=4)[CH2:21][CH2:20][CH2:19]3)[CH2:14][CH2:13]2)=[CH:6][CH:5]=1.O>CO>[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:30])[CH2:11][N:12]2[CH2:13][CH2:14][CH:15]([N:18]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([O:28][CH3:29])[CH:26]=4)[CH2:21][CH2:20][CH2:19]3)[CH2:16][CH2:17]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 18516076HCID 18516076, compound

Product 1

HCID 22038239HCID 22038239, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (73 mg) was added at 0° C. to a solution of 1-{1-[2-(4-fluorophenyl)-2-oxoethyl]piperidin-4-yl}-7-methoxy-1,2,3,4-tetrahydroquinoline (400 mg) in methanol (10 ml). The resultant mixture was stirred at the same temperature for 1 hr and then at room temperature for 1 hr. After the completion of the reaction, water was added to the reaction solution followed by extraction with ethyl acetate. The resulting residue was purified by column chromatography (hexane/ethyl acetate system) to give 1-{1-[2-(4-fluorophenyl)-2-hydroxyethyl]piperidin-4-yl}-7-methoxy-1,2,3,4-tetrahydroquinoline as an oil. This product was dissolved in ethanol and oxalic acid was added thereto. The resulting precipitate of salt was recrystallized form ethanol/ether to give the title compound (280 mg) (yield: 68%).

Workup

  1. additionwas added to the reaction solution
  2. extractionfollowed by extraction with ethyl acetate
  3. customThe resulting residue was purified by column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-4e1a5fcd05574f2a867f7e9123218cf9
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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