Hydrochloric Acid → HCID 21498908, compound

HRID 1730079Notes

Reaction equation

HRID 1730079 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([C:7](=O)[CH2:8][CH:9]2[C:14](=O)[CH2:13][CH2:12][S:11][CH2:10]2)=[CH:5][CH:4]=1.[CH3:19][N:20]([CH2:22][CH2:23][CH2:24][NH2:25])[CH3:21].C(O)C.[ClH:29]>Cl.CCOCC>[ClH:29].[CH3:19][N:20]([CH3:21])[CH2:22][CH2:23][CH2:24][N:25]1[C:7]([C:6]2[CH:17]=[CH:18][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:8][C:9]2[CH2:10][S:11][CH2:12][CH2:13][C:14]1=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 21498933HCID 21498933, compound

Product 1

HCID 21498908HCID 21498908, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3283Diethyl EtherSolvent

Procedure

A solution of 3.09 g (0.012 mole) of 3-(4-methoxyphenacyl)-2,3,5,6-tetrahydrothiopyran-4-one, 1.22 g of dimethylaminopropylamine, 20 ml. of ethanol and one drop of concentrated hydrochloric acid is heated under reflux for 1.5 hours, cooled to ambient temperature, treated with 4 ml. of saturated ethereal hydrogen chloride, and diluted to the cloud point with ether. A brown solid precipitates. The solid is recrystallized from 2-propanol to give tan crystals of 1-(3-dimethylaminopropyl)-2-(4-methoxyphenyl)-1,4,6,7-tetrahydrothiopyrano[4,3-b]pyrrole hydrochloride, m.p. 193 to 194°C.

Workup

  1. temperatureunder reflux for 1.5 hours
  2. additiontreated with 4 ml
  3. customA brown solid precipitates
  4. customThe solid is recrystallized from 2-propanol

Sources & evidence

ORD record
ord-d24cc0f36f38463eb21320d23b08c789
Source dataset
uspto-grants-1976_11
Patent number
US03991076

Reaction notes

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