Dimethylamine → 2-[2-(Dimethylamino)ethyl]-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-thiazepin-5(4H)-one dihydrochloride

HRID 236177Notes

Reaction equation

HRID 236177 reaction equation
[Cl:1][CH2:2][CH2:3][CH:4]1[CH2:10][N:9]([CH3:11])[C:8](=[O:12])[C:7]2[CH:13]=[CH:14][CH:15]=[N:16][C:6]=2[S:5]1.[CH3:17][NH:18][CH3:19]>>[ClH:1].[ClH:1].[CH3:17][N:18]([CH3:19])[CH2:2][CH2:3][CH:4]1[CH2:10][N:9]([CH3:11])[C:8](=[O:12])[C:7]2[CH:13]=[CH:14][CH:15]=[N:16][C:6]=2[S:5]1

Participants

3

Reactant 2

HCID 674Dimethylamine2×HCID 137264572-(2-Chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-thiazepin-5(4H)-one

Product 1

HCID 137265702-[2-(Dimethylamino)ethyl]-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-thiazepin-5(4H)-one dihydrochloride

Procedure

A solution of 1.5 g (0.0058 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-thiazepin-5(4H)-one in 20 ml of dimethylamine was stirred at 25° C. in a sealed container for 72 hr. The excess dimethylamine was allowed to evaporate and the residue was partitioned between chloroform and dilute sodium hydroxide. The chloroform layer was concentrated and the residue, the free base of the title compound, was dissolved in isopropyl alcohol and reacted with hydrogen chloride. The resulting hydrochloride salt weighed 1.5 g (77%), m.p. >250° C.

Workup

  1. customto evaporate
  2. customthe residue was partitioned between chloroform and dilute sodium hydroxide
  3. concentrationThe chloroform layer was concentrated
  4. dissolutionthe residue, the free base of the title compound, was dissolved in isopropyl alcohol
  5. customreacted with hydrogen chloride

Sources & evidence

ORD record
ord-8e4e33ae237e4a62a7ec2fc8aaff58fa
Source dataset
uspto-grants-1987_02
Patent number
US04642343

Reaction notes

Loading…