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

HRID 364413Notes

Reaction equation

HRID 364413 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-bc1eafd957e8494783f93aea260ccdc9
Source dataset
uspto-grants-1986_08
Patent number
US04604388

Reaction notes

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