Sodium Hydroxide → Cyclopropanecarboxylic Acid 4-chloro-3-cyclopropylaminomethyl-benzylamide

HRID 2428137Notes

Reaction equation

HRID 2428137 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[Cl:5][C:6]1[CH:18]=[CH:17][C:9]([CH2:10][NH:11][C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])=[CH:8][C:7]=1[CH:19]=O.[BH4-].[Na+].[OH-].[Na+]>CO>[Cl:5][C:6]1[CH:18]=[CH:17][C:9]([CH2:10][NH:11][C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])=[CH:8][C:7]=1[CH2:19][NH:4][CH:1]1[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 69828CyclopropylamineHCID 4311764Sodium borohydrideHCID 86632362Cyclopropanecarboxylic Acid 4-chloro-3-formyl-benzylamide

Product 1

HCID 67148597Cyclopropanecarboxylic Acid 4-chloro-3-cyclopropylaminomethyl-benzylamideYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Cyclopropylamine (1.39 mL, 19.8 mmol) was added to a sol. of cyclopropanecarboxylic acid 4-chloro-3-formyl-benzylamide (3.13 g, 13.2 mmol) in MeOH (28 mL). The mixture was stirred overnight, and NaBH4 (996 mg, 26.0 mmol) was added in portions. The mixture was stirred for 3 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 (3.37 g, 92%). LC-MS: tR=0.62 min; ES+: 279.35.

Workup

  1. stirringThe mixture was stirred for 3 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-e602315cf0c8433b8c7f84c71a7880f7
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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