Sodium borohydride → 4-[3-(2-Hydroxymethylbenzoyl)aminopropyloxy]pyridine

HRID 6150Notes

Reaction equation

HRID 6150 reaction equation
[BH4-].[Na+].[C:3]1(=[O:23])[N:7]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[C:6](=[O:18])[C:5]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:4]12>C(O)C>[OH:23][CH2:3][C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[C:6]([NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=1)=[O:18]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 190790904-(3-Phthalimidopropyloxy)pyridine

Product 1

HCID 190791834-[3-(2-Hydroxymethylbenzoyl)aminopropyloxy]pyridineYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride [3.78 g (100 mmol)] was added to a solution of 2.82 g (10.0 mmol) of 4-(3-phthalimidopropyloxy)pyridine in 150 ml of ethanol. The mixture was stirred at room temperature for 3 hours. After the solvent was distiled off, brine was added to the residue. The mixture was extracted with chloroform and dried over anhydrous magnesium sulfate. The solvent was distilled off and then the residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:10) to obtain 1.488 g of the desired compound (yield: 52.0%, colorless crystals).

Workup

  1. customAfter the solvent was distiled off
  2. additionbrine was added to the residue
  3. extractionThe mixture was extracted with chloroform
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:10)

Sources & evidence

ORD record
ord-4dbf302df4464d14a210fcb5a6554452
Source dataset
uspto-grants-1993_09
Patent number
US05246948

Reaction notes

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