Chloroacetaldehyde → HCID 67064917, compound

HRID 535788Notes

Reaction equation

HRID 535788 reaction equation
[C:1]1([C@@H:7]2[CH2:9][C@H:8]2[NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:11][CH2:12][CH:13]=O.[BH3-]C#N.[Na+]>[NH4+].[Cl-]>[Cl:11][CH2:12][CH2:13][NH:10][C@@H:8]1[CH2:9][C@H:7]1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 19493(1R,2S)-TranylcypromineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 67064917HCID 67064917, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

The (trans)-2-phenylcyclopropanamine previously obtained was added to activated and dried molecular sieves (3 A), proceeding with several vacuum and argon cycles. DCM (120 mL) was added and stirred before adding chloroacetaldehyde (1.5 mL, 12.0 mmol) and stirring for 4 hours. The reaction was cooled to 0° C. and NaBH3CN (0.88 g, 14.0 mmol) was added. The mixture was stirred at room temperature overnight. NH4Cl (20 mL) was added and the organic layer was extracted, dried with MgSO4 and filtered. The crude was purified by silica gel chromatography (Hexane-MTBE 70:30) affording 1.68 g (8.56 mmol) of N-(2-chloroethyl)-N-[(trans)-2-phenylcyclopropyl]amine. Yield: 72%. 1HNMR (CDCl3) δ (ppm): 1.01 (q, 1H), 1.08 (quin, 1H), 1.93 (m, 1H), 2.37 (quin, 1H), 3.08 (t, 2H), 3.67 (t, 2H), 7.04 (d, 2H), 7.15 (t, 1H), 7.25 (t, 2H). MS (M+H): 195.88

Workup

  1. additionwas added
  2. customdried molecular sieves (3 A),
  3. additionDCM (120 mL) was added
  4. stirringstirring for 4 hours
  5. stirringThe mixture was stirred at room temperature overnight
  6. extractionthe organic layer was extracted
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. customThe crude was purified by silica gel chromatography (Hexane-MTBE 70:30)

Sources & evidence

ORD record
ord-ff23d96ce4174384b9d8612039ef0e1d
Source dataset
uspto-grants-2014_10
Patent number
US08859555B2

Reaction notes

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