Cyclopropylamine → HCID 67148565, compound

HRID 2428145Notes

Reaction equation

HRID 2428145 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([NH:12][CH3:13])=[O:11])=[CH:4][C:3]=1[CH:14]=O.[CH:16]1([NH2:19])[CH2:18][CH2:17]1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([NH:12][CH3:13])=[O:11])=[CH:4][C:3]=1[CH2:14][NH:19][CH:16]1[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 69828Cyclopropylamine2×HCID 4311764Sodium borohydrideHCID 86632364HCID 86632364, compound

Product 1

HCID 67148565HCID 67148565, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-(4-chloro-3-formyl-phenyl)-N-methyl-propionamide (2.30 g, 10.2 mmol) and cyclopropylamine (1.09 mL, 15.3 mmol) in MeOH (109 mL) was stirred for 2 h. Cyclopropylamine (0.364 mL, 5.09 mmol) was added, and the mixture was heated to reflux for 4 h. The mixture was allowed to cool down to rt, and NaBH4 (771 mg, 20.4 mmol) was added by portion. The mixture was stirred for 2 h at rt. The solvents were removed under reduced pressure, and the resulting oil was diluted with EtOAc (500 mL). 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 (MeOH/CH2Cl2 5:95) yielded the title compound (2.05 g, 75%). LC-MS: tR=0.58 min; ES+: 267.39.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 h
  3. stirringThe mixture was stirred for 2 h at rt
  4. customThe solvents were removed under reduced pressure
  5. additionthe resulting oil was diluted with EtOAc (500 mL)
  6. washThe resulting mixture was washed with aq. sat. NaHCO3 and brine
  7. dry with materiallayer was dried over MgSO4
  8. filtrationfiltered
  9. customthe solvents were removed under reduced pressure
  10. customPurification of the crude by FC (MeOH/CH2Cl2 5:95)

Sources & evidence

ORD record
ord-bc3cf84512254577a48b482ab69e908d
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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