N,N-Dimethyl-1,3-propanediamine → HCID 21498923, compound

HRID 1730073Notes

Reaction equation

HRID 1730073 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([C:6](=O)[CH2:7][CH:8]2[C:13](=O)[CH2:12][CH2:11][S:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:18][N:19]([CH3:24])[CH2:20][CH2:21][CH2:22][NH2:23]>Cl.C(O)C>[CH3:18][N:19]([CH3:24])[CH2:20][CH2:21][CH2:22][N:23]1[C:6]([C:5]2[CH:16]=[CH:17][C:2]([Br:1])=[CH:3][CH:4]=2)=[CH:7][C:8]2[CH2:9][S:10][CH2:11][CH2:12][C:13]1=2

Participants

5

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 21498918HCID 21498918, compound

Product 1

HCID 21498923HCID 21498923, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

A solution of 60 g (0.019 mole) of 3-(4-bromophenacyl)-2,3,5,6-tetrahydrothiopyran-4-one, 1.97 g of 3-dimethylaminopropylamine, 20 ml. of ethanol, and one drop of concentrated hydrochloric acid is heated under reflux under nitrogen for 2.5 hours and allowed to stand overnight during which time crystals precipitated. Recrystallization from ethanol gives colorless crystals of 1-(3-dimethylaminopropyl)-2-(4-bromophenyl)-1,4,6,7-tetrahydrothiopyrano[4,3-b]-pyrrole, m.p. 88° to 90°C.

Workup

  1. temperatureunder reflux under nitrogen for 2.5 hours
  2. customprecipitated
  3. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-3b5ed0d5fffd4e29b55e53ded3f3bd8c
Source dataset
uspto-grants-1976_11
Patent number
US03991076

Reaction notes

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