Sodium Hydroxide → N-(4-chloro-3-cyclopropylaminomethylbenzyl)propionamide

HRID 2428133Notes

Reaction equation

HRID 2428133 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[Cl:5][C:6]1[CH:17]=[CH:16][C:9]([CH2:10][NH:11][C:12](=[O:15])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH:18]=O.[BH4-].[Na+].[OH-].[Na+]>CO>[Cl:5][C:6]1[CH:17]=[CH:16][C:9]([CH2:10][NH:11][C:12](=[O:15])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH2:18][NH:4][CH:1]1[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 69828CyclopropylamineHCID 4311764Sodium borohydrideHCID 86632361N-(4-chloro-3-formylbenzyl)propionamide

Product 1

HCID 67148410N-(4-chloro-3-cyclopropylaminomethylbenzyl)propionamideYield 81.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Cyclopropylamine (1.28 mL, 18.2 mmol) was added to a sol. of N-(4-chloro-3-formyl-benzyl)-propionamide (2.74 g, 12.1 mmol) in MeOH (42 mL). The mixture was stirred overnight, and NaBH4 (918 mg, 24.3 mmol) was added in portions. The mixture was stirred for 4 h, and aq. 1M NaOH (70 mL) was added. The solvents were partially removed under reduced pressure, and the aq. residue was extracted with EtOAc (2×). The combined org. extracts were washed with brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC(CH2Cl2→MeOH/CH2Cl2 1:9) yielded the title compound (2.62 g, 81%). LC-MS: tR=0.58 min; ES+: 267.38.

Workup

  1. stirringThe mixture was stirred for 4 h
  2. customThe solvents were partially removed under reduced pressure
  3. extractionthe aq. residue was extracted with EtOAc (2×)
  4. washextracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure
  8. customPurification of the crude by FC(CH2Cl2→MeOH/CH2Cl2 1:9)

Sources & evidence

ORD record
ord-e9daf6c0b4834effbe5bc597ad5eca2d
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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