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Formaldehyde → Alpha-isopropyl-alpha-[3-[N-[3-(3-hydroxymethylphenoxy)propyl]-N-methylamino]propyl]-3,4,5-trimethoxyphenylacetonitrile

HRID 65096
Notes
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Reaction equation

HRID 65096 reaction equation
[CH:1]([C:4]([C:23]1[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=1)([CH2:7][CH2:8][CH2:9][NH:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][OH:22])[CH:16]=1)[C:5]#[N:6])([CH3:3])[CH3:2].[CH2:35]=O.[BH4-].[Na+]>CO>[CH:1]([C:4]([C:23]1[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=1)([CH2:7][CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][OH:22])[CH:16]=1)[CH3:35])[C:5]#[N:6])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 13714914HCID 13714914, compound

Product 1

HCID 13714731Alpha-isopropyl-alpha-[3-[N-[3-(3-hydroxymethylphenoxy)propyl]-N-methylamino]propyl]-3,4,5-trimethoxyphenylacetonitrileYield 25.7%

Reagents, catalysts & solvents 1

HCID 887Methanol
Solvent

Procedure

A solution of 2.80 g of alpha-isopropyl-alpha-[3-[N-[3-(3-hydroxymethylphenoxy)propyl]amino]propyl]-3,4,5-trimethoxyphenyl acetonitrile and 4.84 g of 37% formalin in 70 ml of methanol was refluxed for 1 hour. After cooling, to the solution was added 2.25 g of sodium borohydride and the solution was stirred for 1 hour at room temperature. The solvent was removed and to the residue was added water. The solution was extracted with chloroform and the extract was washed with water, dried, and evaporated. The residue was chromatographed on silica gel using 10% methanol-chloroform as an eluent to give 0.74 g of the desired compound as a yellow oil.

Workup

  1. temperatureAfter cooling, to the solution
  2. customThe solvent was removed and to the residue
  3. additionwas added water
  4. extractionThe solution was extracted with chloroform
  5. washthe extract was washed with water
  6. customdried
  7. customevaporated
  8. customThe residue was chromatographed on silica gel using 10% methanol-chloroform as an eluent

Sources & evidence

ORD record
ord-8b99c9550e4f4c0fbace963d499632eb
Source dataset
uspto-grants-1986_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04612329

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes