Cyclopropanecarboxaldehyde → N-(Cyclopropyhnethyl)-N-{2-[4-(3,4-difluorophenoxy)-1-piperidinyl]ethyl}amine

HRID 968761Notes

Reaction equation

HRID 968761 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[F:18])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][NH2:14])[CH2:8][CH2:7]1.[CH:19]1([CH:22]=O)[CH2:21][CH2:20]1>CO>[CH:19]1([CH2:22][NH:14][CH2:13][CH2:12][N:9]2[CH2:8][CH2:7][CH:6]([O:5][C:4]3[CH:15]=[CH:16][C:17]([F:18])=[C:2]([F:1])[CH:3]=3)[CH2:11][CH2:10]2)[CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 123114CyclopropanecarboxaldehydeHCID 693106352-[4-(3,4-Difluorophenoxy)-1-piperidinyl]ethylamine

Product 1

HCID 70015962N-(Cyclopropyhnethyl)-N-{2-[4-(3,4-difluorophenoxy)-1-piperidinyl]ethyl}amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product of Step d (0.4 g) dissolved in MeOH (6 ml) was added to cyclopropanecarbaldehyde (0.116 ml) and the resulting mixture was stirred for 4 hours. The solvent was evaporated, the residue re-dissolved in methanol (6 ml) and NaBH4 (0.095 g) added and the mixture left for 30 minutes. Aqueous sodium hydroxide (1N) was added and the aqueous extracted with diethyl ether. The organic extracts were dried with Na2SO4, filtered and concentrated to give the sub-title product as an oil (0.493 g).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue re-dissolved in methanol (6 ml)
  3. additionNaBH4 (0.095 g) added
  4. waitthe mixture left for 30 minutes
  5. additionAqueous sodium hydroxide (1N) was added
  6. extractionthe aqueous extracted with diethyl ether
  7. dry with materialThe organic extracts were dried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-331e1f71b3e442c1bc4d25e8a8cec63a
Source dataset
uspto-grants-2007_12
Patent number
US07304077B2

Reaction notes

Loading…