Hydrochloric Acid → 6-{1-Hydroxy-4-[bis-chloroethyl-amino]butyl}-3,4-dihydrocarbostyril

HRID 1285441Notes

Reaction equation

HRID 1285441 reaction equation
[O:1]=[C:2]([C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18](=[O:23])[CH2:17][CH2:16]2)[CH2:3][CH2:4][CH2:5][N:6]([CH2:10][CH2:11][Cl:12])[CH2:7][CH2:8][Cl:9].[BH4-].[Na+].Cl.[OH-].[Na+]>CO.O>[OH:1][CH:2]([C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18](=[O:23])[CH2:17][CH2:16]2)[CH2:3][CH2:4][CH2:5][N:6]([CH2:10][CH2:11][Cl:12])[CH2:7][CH2:8][Cl:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 202294206-{1-Oxo-4-[di-(2-chloroethyl)-amino]butyl}-3,4-dihydrocarbostyril

Product 1

HCID 202294566-{1-Hydroxy-4-[bis-chloroethyl-amino]butyl}-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2.5 Grams of 6-{1-oxo-4-[di-(2-chloroethyl)-amino]butyl}-3,4-dihydrocarbostyril was dissolved in 80 ml of methanol, with stirring at a room temperature condition 1.6 g of sodium borohydride was added gradually to the mixture in 15 minutes and further stirred at a room temperature for 2 hours. To the reaction mixture was added 5 ml of concentrated hydrochloric acid was added and the reaction mixture was concentrated under a reduced pressure to dryness. The residue thus obtained was dissolved in 10 ml of water, the pH of the solution was adjusted to 6-7 by adding 2N-sodium hydroxide aqueous solution and stirred to precipitate crystals. The crystals were collected by filtration washed with water and dried to obtain 1.4 g of 6-{1-hydroxy-4-[bis(2-chloroethyl)amino]-butyl}-3,4-dihydrocarbostyril in colorless powdery product.

Workup

  1. additionwas added gradually to the mixture in 15 minutes
  2. additionwas added
  3. concentrationthe reaction mixture was concentrated under a reduced pressure to dryness
  4. customThe residue thus obtained
  5. stirringstirred
  6. customto precipitate crystals
  7. filtrationThe crystals were collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-382d5b18491a49d0a5dc794474c55aed
Source dataset
uspto-grants-1986_01
Patent number
US04567187

Reaction notes

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