Sodium borohydride → Indoramin

HRID 971953Notes

Reaction equation

HRID 971953 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 (7.3 kg.) and sodium borohydride (2.5 kg.) in isopropanol (57 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 4.45 kg. of the crude title compound. This was purified by dissolving in dimethylformamide (21 kg.) at 50°-60° and slowly adding water (22 kg.). After cooling, the product was separated by filtration, washed with water then with methanol, and dried to give 3.9 kg. of the title compound (65% 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 4.45 kg

Sources & evidence

ORD record
ord-314aacfeb14e48d5b41d46a333948a1c
Source dataset
uspto-grants-1979_07
Patent number
US04162252

Reaction notes

Loading…