Sodium borohydride → Indoramin

HRID 971954Notes

Reaction equation

HRID 971954 reaction equation
[Br-].[C:2]([NH:10][C:11]1[CH:16]=[CH:15][N+:14]([CH2:17][CH2:18][C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)=[CH:13][CH:12]=1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BH4-].[Na+]>C(O)(C)C.O>[C:2]([NH:10][CH:11]1[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)[CH2:15][CH2:16]1)(=[O:9])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 18177187HCID 18177187, compound

Product 1

HCID 33625Indoramin

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A suspension of 4-benzamido-1-[2-(3-indolyl)ethyl]-pyridinium bromide (48.7 kg.) and sodium borohydride (17.4 Kg.) in isopropanol (424 kg.) was stirred and refluxed for 6 hours. The reaction mixture was cooled to 25° and diluted with water. The product was separated by filtration and washed with aqueous methanol then with water and finally with methanol, and dried to give 40.7 kg. of the crude title compound. This was purified by dissolving in dimethylformamide (193 kg.) at 50°-60° and slowly adding water (220 kg.) to the filtered solution. After cooling, the product was separated by filtration, washed with water then with methanol, and dried to give 30.3 kg. of the title compound (75.5% yield).

Workup

  1. temperaturerefluxed for 6 hours
  2. temperatureThe reaction mixture was cooled to 25°
  3. customThe product was separated by filtration
  4. washwashed with aqueous methanol
  5. dry with materialwith water and finally with methanol, and dried
  6. customto give 40.7 kg

Sources & evidence

ORD record
ord-e2ba6bfd89c142c48cc80d4bc949c9a3
Source dataset
uspto-grants-1979_07
Patent number
US04162252

Reaction notes

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