Water → HCID 67249157, compound

HRID 2175094Notes

Reaction equation

HRID 2175094 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][N:10]([C:13]2[N:18]=[C:17]([C:19]3[CH:28]=[C:27]4[C:22]([C:23]([CH3:31])([CH3:30])[CH2:24][CH2:25][C:26]4=[O:29])=[CH:21][CH:20]=3)[CH:16]=[CH:15][CH:14]=2)[CH2:9][CH2:8]1.[BH4-].[Na+].O>C1COCC1.CO>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([C:13]2[N:18]=[C:17]([C:19]3[CH:28]=[C:27]4[C:22]([C:23]([CH3:31])([CH3:30])[CH2:24][CH2:25][CH:26]4[OH:29])=[CH:21][CH:20]=3)[CH:16]=[CH:15][CH:14]=2)[CH2:11][CH2:12]1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 53251220HCID 53251220, compound

Product 1

HCID 67249157HCID 67249157, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

50 mg (0.12 mmol) of 7-{6-[4-(5-hydroxypentyl)piperazin-1-yl]pyridin-2-yl}-4,4-dimethyl-3,4-dihydro-2H-naphthalen-1-one are dissolved in 0.5 ml of THF and 1 ml of methanol, cooled to 0° C., and 4.5 mg (0.12 mmol) of sodium borohydride are added. The reaction mixture is stirred for 30 min, water is added, and the mixture is extracted with ethyl acetate, dried and evaporated. The crude product is purified by means of prep HPLC and subsequently converted into the hydrochloride using methanolic HCl.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. customdried
  3. customevaporated
  4. customThe crude product is purified by means of prep HPLC

Sources & evidence

ORD record
ord-d231d18d6bf244db962619e5995f825d
Source dataset
uspto-grants-2015_06
Patent number
US09062015B2

Reaction notes

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