Formaldehyde → HCID 22406756, compound

HRID 440509Notes

Reaction equation

HRID 440509 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH:11]2[C:20]3[C:15](=[CH:16][C:17]([CH3:23])=[C:18]([O:21][CH3:22])[CH:19]=3)[CH2:14][CH2:13][NH:12]2)[CH2:10][CH2:9]1.CO.C=O.[C:28]([BH3-])#N.[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH:11]2[C:20]3[C:15](=[CH:16][C:17]([CH3:23])=[C:18]([O:21][CH3:22])[CH:19]=3)[CH2:14][CH2:13][N:12]2[CH3:28])[CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 22406819HCID 22406819, compound

Product 1

HCID 22406756HCID 22406756, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-[1-(2-chlorophenyl)cyclopropyl]-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline (6.2 g), methanol (160 ml) and 37-40% aqueous formaldehyde solution was stirred for 15 minutes. Sodium cyanoborohydride (5.13 g) was added and the mixture was stirred for a further 10 minutes. The reaction was then neutralised with acetic acid and stirred for 45 minutes. The methanol was removed in vacuo and the residue treated with aqueous sodium hydroxide solution. The product was extracted with ethyl acetate. The extracts were washed with aqueous ammonia solution, water and brine, then dried over magnesium sulphate. Concentration yielded 1-[1-(2-chlorophenyl)cyclopropyl]-7-methoxy-2,6-dimethyl-1,2,3,4-tetrahydroisoquinoline as a gum (5.02 g).

Workup

  1. stirringthe mixture was stirred for a further 10 minutes
  2. stirringstirred for 45 minutes
  3. customThe methanol was removed in vacuo
  4. additionthe residue treated with aqueous sodium hydroxide solution
  5. extractionThe product was extracted with ethyl acetate
  6. washThe extracts were washed with aqueous ammonia solution, water and brine
  7. dry with materialdried over magnesium sulphate
  8. concentrationConcentration

Sources & evidence

ORD record
ord-4ea6574fb06c4d43a700a9f54d98acd4
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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