Cyclopropylamine → HCID 67148433, compound

HRID 1715410Notes

Reaction equation

HRID 1715410 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][NH:7][C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[CH:13]=O.[CH:15]1([NH2:18])[CH2:17][CH2:16]1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][NH:7][C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[CH2:13][NH:18][CH:15]1[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 4311764Sodium borohydrideHCID 86622957HCID 86622957, compound

Product 1

HCID 67148433HCID 67148433, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-(4-chloro-3-formyl-benzyl)-acetamide (382 mg, 1.81 mmol) and cyclopropylamine (0.194 mL, 2.71 mmol) in MeOH (18 mL) was heated to reflux for 4 h. The mixture was allowed to cool to rt, and NaBH4 (102 mg, 2.71 mmol) was added in portions. The mixture was stirred for 1 h, and the solvents were removed under reduced pressure. EtOAc (50 mL) was added, and the resulting mixture was washed with aq. sat. NaHCO3 and brine. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (CH2Cl2/MeOH 95:5) yielded the title compound (371 mg, 81%). LC-MS: tR=0.53 min; ES+: 253.11.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. customthe solvents were removed under reduced pressure
  4. additionEtOAc (50 mL) was added
  5. washthe resulting mixture was washed with aq. sat. NaHCO3 and brine
  6. dry with materiallayer was dried over MgSO4
  7. filtrationfiltered
  8. customthe solvents were removed under reduced pressure
  9. customPurification of the crude by FC (CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-0a718c928e5249e7a88da743b0eb671d
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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