Hydrochloric Acid → Tolvaptan

HRID 1486485Notes

Reaction equation

HRID 1486485 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:30])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:28])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH3:27])=[CH:15][C:14]=3[CH3:29])[CH2:10][CH2:9][CH2:8][C:7](=[O:31])[C:6]=2[CH:32]=1.O.[BH4-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:30])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:28])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH3:27])=[CH:15][C:14]=3[CH3:29])[CH2:10][CH2:9][CH2:8][CH:7]([OH:31])[C:6]=2[CH:32]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 113628435-Dehydro Tolvaptan

Product 1

HCID 216237TolvaptanYield 89.23%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-chloro-1-[2-methyl-4-(2-methyl benzoyl amino) benzoyl]-5 oxo-2,3,4,5-tetrahydro-1H-1-benzazepine (6.5 gm.) was suspended in methanol (104 ml) & water (10.4 ml) and then added sodium borohydride (0.385 gm.) at 30° C. and the reaction mixture was stirred for 1 hr. To the reaction mixture was added hydrochloric acid (39 ml). Then the reaction mixture was stirred for 2 hours. The solid obtained was collected by filtration and dried to give 7-chloro-5-hydroxy-1-[2-methyl-4-(2-methyl benzoyl amino) benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine (5.8 gm.).

Workup

  1. customThe solid obtained
  2. filtrationwas collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-2da2819c285745ca98622190da4664ce
Source dataset
uspto-grants-2016_08
Patent number
US09428461B2

Reaction notes

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