Sodium borohydride → HCID 18930333, compound

HRID 1450434

Reaction equation

HRID 1450434 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:14][CH2:13]1)=[O:11].[BH4-].[Na+]>CO>[CH3:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][CH2:18][N:15]2[CH2:14][CH2:13][CH:12]([CH:10]([C:2]3[S:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)[OH:11])[CH2:17][CH2:16]2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 9842862[2-Benzothiazolyl][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl)methanone

Product 1

HCID 18930333HCID 18930333, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve [2-benzothiazolyl][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]methanone (3.0 g, 7.88 mmol) in methanol (150 mL) and cool to 0° C. Add sodium borohydride (597 mg, 15.77 mmol) and stir for 1.5 hours, adding additional sodium borohydride after 30 minutes. Evaporate the solvent in vacuo and partition the residue between water and methylene chloride. Separate the organic phase, wash with saturated sodium chloride, dry (MgSO4) and evaporate the solvent in vacuo. Purify by recrystallization (ethyl acetate) to give the title compound as white fluffy crystals; mp 127°-129° C.

Workup

  1. customEvaporate the solvent in vacuo
  2. custompartition the residue between water and methylene chloride
  3. customSeparate the organic phase
  4. washwash with saturated sodium chloride
  5. dry with materialdry (MgSO4)
  6. customevaporate the solvent in vacuo
  7. customPurify by recrystallization (ethyl acetate)

Sources & evidence

ORD record
ord-5c34649375da43bebb6de88600e00f86
Source dataset
uspto-grants-1997_02
Patent number
US05602147

Linked notes

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