Chloroacetaldehyde → HCID 68882678, compound

HRID 2112400Notes

Reaction equation

HRID 2112400 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:11]=[CH:12][C:13]=2[O:14][CH3:15])[NH2:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:16][CH2:17][CH:18]=O.[BH3-]C#N.[Na+].C(O)(=O)C>CO>[Cl:16][CH2:17][CH2:18][NH:10][C:9]1[CH:11]=[CH:12][C:13]([O:14][CH3:15])=[C:7]([O:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[CH:8]=1

Participants

6

Reactant 4

HCID 33ChloroacetaldehydeHCID 176Acetic AcidHCID 27793343-(Cyclopentyloxy)-4-methoxyanilineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 68882678HCID 68882678, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
15 °C

Procedure

To a solution of 2.15 g (10.4 mmol) 3-cyclopentyloxy-4-methoxyaniline (J. Org. Chem. 2005,70, 1050) in 100 ml methanol were added 2.0 g (14.1 mmol) chloroacetaldehyde solution (55% in water), 3.9 g (62.6 mmol) NaBH3CN and 0.5 ml acetic acid. The reaction was stirred over night at 15° C. and the solvent was subsequently evaporated. The residue was taken up in 120 ml dichloromethane and the organic phase was washed with brine, dried over Na2SO4 and evaporated in vacuo. The crude product was purified by chromatography on silica gel (hexane:ethyl acetate 100:1 then 15:1) to give 1.78 g (63.5%) of the desired product as a yellow oil. 1H-NMR (DMSO): 6.70 (d, 1H), 6.28 (s, 1H), 6.06 (d, 1H), 5.43 (m, 1H), 4.69 (m, 1H), 3.68 (m, 2H), 3.60 (m, 3H), 3.32 (m, 2H), 1.83 (m, 2H), 1.69 (m, 4H), 1.55 (m, 2H).

Workup

  1. customthe solvent was subsequently evaporated
  2. washthe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo
  5. customThe crude product was purified by chromatography on silica gel (hexane:ethyl acetate 100:1

Sources & evidence

ORD record
ord-f6c665fa32a842e2b16770aa233eb19c
Source dataset
uspto-grants-2009_04
Patent number
US07524823B2

Reaction notes

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