Formaldehyde → N-[2-(3,4-Dimethoxyphenyl)ethyl]-4-[5-methoxy-2-(phenylethynyl)phenyl]-N-methylbutan-2-amine

HRID 623164Notes

Reaction equation

HRID 623164 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][CH:14]([CH3:33])[CH2:15][CH2:16][C:17]2[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=2[C:25]#[C:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH2:34]=O.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH3:34])[CH:14]([CH3:33])[CH2:15][CH2:16][C:17]2[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=2[C:25]#[C:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 9980864HCID 9980864, compound2×

Product 1

HCID 127269N-[2-(3,4-Dimethoxyphenyl)ethyl]-4-[5-methoxy-2-(phenylethynyl)phenyl]-N-methylbutan-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of of N-[2-(3,4-dimethoxyphenyl)ethyl]-5-methoxy-α-methyl-2-(phenylethynyl)benzenepropanamine (0.3 g, 0.68 mmole), the free base of the product of Example 1e, and 37% aqueous formaldehyde (0.5 mL) were combined in absolute methanol (5 mL). With stirring, sodium borohydride (0.05 g, 1.3 mmole) was added, and the resulting reaction mixture stirred overnight. The mixture was concentrated in vacuo, the resulting residue dissolved in 5 mL of EtOAc, 5 mL of 1N sodium hydroxide was added and the resulting layers separated. The aqueous layer was extracted with EtOAc and washed with water, brine and dried over anhydrous sodium sulfate. After filtering, the filtrate was concentrated in vacuo to give 0.3 g of the title product as a golden oil. The title product is the antihypertensive pharmaceutical prepared in Example 32 of European Pat. No. 146,271.

Workup

  1. customthe resulting reaction mixture
  2. stirringstirred overnight
  3. concentrationThe mixture was concentrated in vacuo
  4. dissolutionthe resulting residue dissolved in 5 mL of EtOAc
  5. addition5 mL of 1N sodium hydroxide was added
  6. customthe resulting layers separated
  7. extractionThe aqueous layer was extracted with EtOAc
  8. washwashed with water, brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationAfter filtering
  11. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-34e3f5598c0e4819bc8e4a5904d42a5d
Source dataset
uspto-grants-1988_09
Patent number
US04772755

Reaction notes

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