3-Chloro-N,N-dimethyl-1-propanamine → Hydrochloric Acid

HRID 1647685Notes

Reaction equation

HRID 1647685 reaction equation
CC([O-])(C)C.[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([C:17]2[CH:22]([CH2:23][CH3:24])[S:21][C:20](=[O:25])[NH:19][N:18]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16].[Cl:26][CH2:27][CH2:28][CH2:29][N:30]([CH3:32])[CH3:31]>CN(C)C=O.C1(C)C=CC=CC=1>[CH3:31][N:30]([CH3:32])[CH2:29][CH2:28][CH2:27][N:19]1[N:18]=[C:17]([C:11]2[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:9]([O:8][CH3:7])[CH:10]=2)[CH:22]([CH2:23][CH3:24])[S:21][C:20]1=[O:25].[ClH:26]

Participants

7

Reactant 3

HCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 153408225-(3,4-Dimethoxyphenyl)-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-oneHCID 23665647Potassium tert-butoxide

Product 2

HCID 313Hydrochloric AcidHCID 99290633-Dimethylaminopropyl-5-(3,4-dimethoxyphenyl)-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

0.6 g of potassium tert-butylate is added to a solution of 1.5 g of 5-(3,4-dimethoxyphenyl)-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one [obtainable by reacting 1-(3,4-dimethoxyphenyl)-2-bromobutan-1-one with methyl hydrazinethioformate] in 30 ml of dimethylformamide (DMF), and the mixture is stirred for 30 minutes. A solution of 3-chloropropyldimethylamine in toluene is then added and the mixture is boiled for three hours. The solvent is removed in vacuo, and the mixture is worked up as usual to give 3-dimethylaminopropyl-5-(3,4-dimethoxyphenyl)-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one, m.p. 175° (hydrochloride).

Workup

  1. waitthe mixture is boiled for three hours
  2. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-7b90bf00e9e242f18fdb30b4c0d60884
Source dataset
uspto-grants-1995_07
Patent number
US05434149

Reaction notes

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