Water → 2-(4-(3-(4-Chlorophenyl)-1,2,4-thiadiazol-5-yl)piperazin-1-yl)-1-(4-methoxyphenyl)ethanol

HRID 570568Notes

Reaction equation

HRID 570568 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][C:20]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)=[O:21])[CH2:15][CH2:14]3)[S:10][N:9]=2)=[CH:4][CH:3]=1.[BH4-].[Na+].O.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]=[C:11]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH:20]([C:22]4[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=4)[OH:21])[CH2:15][CH2:14]3)[S:10][N:9]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 4311764Sodium borohydrideHCID 711862252-(4-(3-(4-Chlorophenyl)-1,2,4-thiadiazol-5-yl)piperazin-1-yl)-1-(4-methoxyphenyl)ethanone

Product 1

HCID 711865742-(4-(3-(4-Chlorophenyl)-1,2,4-thiadiazol-5-yl)piperazin-1-yl)-1-(4-methoxyphenyl)ethanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(4-(3-(4-chlorophenyl)-1,2,4-thiadiazol-5-yl)piperazin-1-yl)-1-(4-methoxyphenyl)ethanone (75 mg, 175 μmol) and NaBH4 (10 mg, 264 μmol) in THF (5 mL) and MeOH (1 mL) was stirred at RT. Water (5 mL) and 10% aq.Na2CO3 (5 mL) was added and stirred for 10 min. The mixture was extracted with EtOAc; the organic layers were washed with brine (20 mL), dried over Na2SO4, filtered off and concentrated in vacuo.

Workup

  1. stirringstirred for 10 min
  2. extractionThe mixture was extracted with EtOAc
  3. washthe organic layers were washed with brine (20 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered off
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a24e6a5f7bc4b4ab98474d66d43c2b1
Source dataset
uspto-grants-2015_05
Patent number
US09023852B2

Reaction notes

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