Formaldehyde → HCID 178483348, compound

HRID 634767Notes

Reaction equation

HRID 634767 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[CH2:20][CH2:19][C@H:18]([NH:21][CH2:22][CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:31]=O.[BH4-].[Na+]>CO>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[CH2:16][CH2:17][C@H:18]([N:21]([CH3:31])[CH2:22][CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:19][CH2:20]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 178420266HCID 178420266, compound

Product 1

HCID 178483348HCID 178483348, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of trans-[4-(4-benzyloxy-phenyl)-cyclohexyl]-(3-phenyl-propyl)-amine (0.4 g, 1.0 mmol), 36.5% aq. formaldehyde (0.12 ml) and MeOH (7 ml) was stirred overnight at RT. Excess sodium borohydride was then added, and stirring was continued for 2 h. Evaporation of the solvent, addition of H2O, extraction with CH2Cl2, drying of the organic layer with Na2SO4, evaporation of the solvent and purification of the residue by chromatography over SiO2 (Merck 230-400 mesh) eluting with CH2Cl2—MeOH—25% aq. NH3 140:10:1 trans-[4-(4-benzyloxy-phenyl)-cyclohexyl]-methyl-(3-phenyl-propyl)-amine (0.41 g, 99%) as a colorless oil. MS: m/e=413 (M+).

Workup

  1. stirringstirring
  2. waitwas continued for 2 h
  3. customEvaporation of the solvent, addition of H2O, extraction with CH2Cl2
  4. dry with materialdrying of the organic layer with Na2SO4, evaporation of the solvent and purification of the residue by chromatography over SiO2 (Merck 230-400 mesh)
  5. washeluting with CH2Cl2—MeOH—25% aq. NH3 140:10:1 trans-[4-(4-benzyloxy-phenyl)-cyclohexyl]-methyl-(3-phenyl-propyl)-amine (0.41 g, 99%) as a colorless oil

Sources & evidence

ORD record
ord-e2ec873c16c9411598b9bcb7b1a2aa67
Source dataset
uspto-grants-2001_02
Patent number
US06184236B2

Reaction notes

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