Formaldehyde → HCID 22406746, compound

HRID 440523Notes

Reaction equation

HRID 440523 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH:12]2[C:21]3[C:16](=[CH:17][C:18]([CH3:24])=[C:19]([O:22][CH3:23])[CH:20]=3)[CH2:15][CH2:14][NH:13]2)[CH2:11][CH2:10][CH2:9]1.C=O.[C:27]([BH3-])#N.[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH:12]2[C:21]3[C:16](=[CH:17][C:18]([CH3:24])=[C:19]([O:22][CH3:23])[CH:20]=3)[CH2:15][CH2:14][N:13]2[CH3:27])[CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 22406903HCID 22406903, compound

Product 1

HCID 22406746HCID 22406746, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

A mixture of the oxalate salt of 1-[1-(2-chlorophenyl)cyclobutyl]-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline (4.42 g prepared as described in Example RC12), methanol (87 ml) and 37-40% aqueous formaldehyde solution (5.1 ml) was cooled to 10° C. and sodium cyanoborohydride (2.64 g) was added. After 10 minutes the mixture was allowed to warm to ambient temperature and was stirred for 24 hours. The reaction mixture was concentrated and the residue partitioned between ethyl acetate and dilute aqueous sodium hydroxide solution. The organic phase was washed with aqueous ammonia solution, then dried and concentrated to yield 1-[1-(2-chlorophenyl)cyclobutyl]-7-methoxy-2,6-dimethyl-1,2,3,4-tetrahydroisoquinoline (3.3 g).

Workup

  1. temperatureto warm to ambient temperature
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue partitioned between ethyl acetate and dilute aqueous sodium hydroxide solution
  4. washThe organic phase was washed with aqueous ammonia solution
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1108f0bb1b9c46edaff0863ad40e27c4
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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