Chloroacetaldehyde → HCID 67065023, compound

HRID 535806Notes

Reaction equation

HRID 535806 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)=[CH:13][C:12]([C@@H:25]2[CH2:27][C@H:26]2[NH2:28])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:29][CH2:30][CH:31]=O>C(Cl)Cl>[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:17][CH:16]=2)=[CH:13][C:12]([C@@H:25]2[CH2:27][C@H:26]2[NH:28][CH2:31][CH2:30][Cl:29])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 70945011HCID 70945011, compound

Product 1

HCID 67065023HCID 67065023, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (trans)-2-(6-(benzyloxy)-4′-(trifluoromethyl)biphenyl-3-yl)cyclopropanamine (520 mg, 2.08 mmol) in DCM (6 mL), 4° A molecular sieves was added followed by chloroacetaldehyde (0.33 mL, 2.5 mmol) and stirred at RT for 1 h. After completion, monitored by TLC, the reaction mixture was cooled at −10° C. and Na(CN)BH3 (157 mg, 2.5 mmol) was added and stirred at RT for 2 h. After completion, the reaction mixture was quenched with NH4Cl (5%) and filtered through a pad of celite. The filtrate was extracted with DCM (2×20 mL), combined extracts were washed with water (20 mL), dried over anhydrous Na2SO4, filtered and evaporated. The residue was purified by flash column chromatography by using EtOAc: Pet ether to get (trans)-2-(6-(benzyloxy)-4′-(trifluoromethyl)biphenyl-3-yl)-N-(2-chloroethyl)cyclopropanamine (500 mg, 83.3%) as a liquid.

Workup

  1. temperaturethe reaction mixture was cooled at −10° C.
  2. stirringstirred at RT for 2 h
  3. customAfter completion, the reaction mixture was quenched with NH4Cl (5%)
  4. filtrationfiltered through a pad of celite
  5. extractionThe filtrate was extracted with DCM (2×20 mL)
  6. washwere washed with water (20 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-42aeecc9d9af40719714ed918796878e
Source dataset
uspto-grants-2014_10
Patent number
US08859555B2

Reaction notes

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