Sodium borohydride → HCID 19045248, compound

HRID 1591215Notes

Reaction equation

HRID 1591215 reaction equation
[ClH:1].Cl.[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:28](=[CH:29][C:30]=1[O:31][CH3:32])[CH:27]=[N:26][C:9]1([CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=3)[CH2:11][CH2:10]1)[CH2:8]2.[BH4-].[Na+]>CO>[ClH:1].[ClH:1].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:28](=[CH:29][C:30]=1[O:31][CH3:32])[CH2:27][NH:26][C:9]1([CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]3[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=3)[CH2:11][CH2:10]1)[CH2:8]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19045237HCID 19045237, compound

Product 1

HCID 19045248HCID 19045248, compoundYield 163.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6,7-dimethoxy-1'-[2-(4-nitrophenyl)ethyl]-spiro[3,4-dihydroisoquinoline-3,4'-piperidine]dihydrochloride (100 mg) in methanol (6 ml) at 0° C. was added NaBH4 (23.8 mg). The reaction was stirred for 15 min. The aqueous solution was extracted with methylene chloride (2×50 ml). The methylene chloride layers were dried over Na2SO4, concentrated to an oil and redissolved in ethanol. Addition of HCL/diethyl ether gave a solid which was filtered, and dried to yield 0.082 g of the title compound. MP 247°-250° C. (Dec).

Workup

  1. extractionThe aqueous solution was extracted with methylene chloride (2×50 ml)
  2. dry with materialThe methylene chloride layers were dried over Na2SO4
  3. concentrationconcentrated to an oil
  4. dissolutionredissolved in ethanol
  5. additionAddition of HCL/diethyl ether
  6. customgave a solid which
  7. filtrationwas filtered
  8. customdried

Sources & evidence

ORD record
ord-d364611713ce4c52ac54008a6ab6e851
Source dataset
uspto-grants-1993_04
Patent number
US05206240

Reaction notes

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