Hydrochloric Acid → HCID 21498927, compound

HRID 1730071Notes

Reaction equation

HRID 1730071 reaction equation
[CH2:1]([CH:10]1[C:15](=O)[CH2:14][CH2:13][S:12][CH2:11]1)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=O.[CH3:17][N:18]([CH3:23])[CH2:19][CH2:20][CH2:21][NH2:22].C(O)C.[ClH:27]>Cl.CCOCC>[ClH:27].[CH3:17][N:18]([CH3:23])[CH2:19][CH2:20][CH2:21][N:22]1[C:2]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[CH:1][C:10]2[CH2:11][S:12][CH2:13][CH2:14][C:15]1=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 21498935HCID 21498935, compound

Product 1

HCID 21498927HCID 21498927, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3283Diethyl EtherSolvent

Procedure

A solution of 3.0 g (0.013 mole) of 3-phenacyl-2,3,5,6-tetrahydrothiopyran-4-one, 1.33 g of 3-dimethylaminopropylamine, 20 ml. of ethanol, and one drop of concentrated hydrochloric acid is heated under reflux under nitrogen for 1.5 hours, and then cooled to ambient temperature. The reaction mixture is treated with 4 ml. of saturated ethereal hydrogen chloride and diluted to the cloud point with ether. The solid which separates is collected and recrystallized from ethanol to provide colorless crystals of 1-(3-dimethylaminopropyl)-2-phenyl-1,4,6,7-tetrahydrothiopyrano[4,3-b]pyrrole hydrochloride, m.p. 225° to 227° C. dec.

Workup

  1. temperatureunder reflux under nitrogen for 1.5 hours
  2. additionThe reaction mixture is treated with 4 ml
  3. customThe solid which separates is collected
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-d532b59410f44767847c34a53cc06769
Source dataset
uspto-grants-1976_11
Patent number
US03991076

Reaction notes

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