Triethylamine → HCID 67148644, compound

HRID 2428113Notes

Reaction equation

HRID 2428113 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:13])[CH3:12])=[CH:4][C:3]=1[CH:14]=O.CCN(CC)CC.[CH:23]1([NH2:26])[CH2:25][CH2:24]1.[BH4-].[Na+].C([O-])(O)=O.[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:13])[CH3:12])=[CH:4][C:3]=1[CH2:14][NH:26][CH:23]1[CH2:25][CH2:24]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 69828CyclopropylamineHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 86622962HCID 86622962, compound

Product 1

HCID 67148644HCID 67148644, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-[2-(4-chloro-3-formyl-phenyl)-ethyl]-acetamide (50.1 mg, 0.222 mmol), Et3N (0.046 mL, 0.332 mmol) and cyclopropylamine (0.023 mL, 0.332 mmol) in MeOH (0.50 mL) was heated to reflux for 4 h. The mixture was allowed to cool to rt, and NaBH4 (21.0 mg, 0.554 mmol) was added in portions. The mixture was stirred for 1 h, and aq. sat. NaHCO3 was added. The mixture was extracted with EtOAc several times, and the combined org. extracts were washed with brine. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC(CH2Cl2/MeOH 95:5) yielded the title compound (35 mg, 59%). LC-MS: tR=0.59 min; ES+: 267.17.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. extractionThe mixture was extracted with EtOAc several times
  4. washextracts were washed with brine
  5. dry with materiallayer was dried over MgSO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure
  8. customPurification of the residue by FC(CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-e15ee31286624b3b8c676de1f1059859
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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