Hydrochloric Acid → HCID 21498911, compound

HRID 1730077Notes

Reaction equation

HRID 1730077 reaction equation
[F: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].C(O)C.[ClH:28]>CCOCC>[ClH:28].[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]([F:1])=[CH:3][CH:4]=2)=[CH:7][C:8]2[CH2:9][S:10][CH2:11][CH2:12][C:13]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 21498936HCID 21498936, compound

Product 1

HCID 21498911HCID 21498911, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4.0 g (0.016 mole) of 3-(4-fluorophenacyl)-2,3,5,6-tetrahydrothiopyran-4-one [Example 5 (a)], 1.62 g of 3-dimethylaminopropylamine and 40 ml. of ethanol is heated under reflux for 2.5 hours, cooled, treated with 4 ml. of saturated ethereal hydrogen chloride, warmed to boiling, and diluted to the cloud point with ether. Upon cooling a solid separates. Recrystallization from ethanol gives off-white crystals of 1-(3-dimethylaminopropyl)-2-(4-fluorophenyl)-1,4,6,7-tetrahydrothiopyrano[4,3-b]pyrrole hydrochloride, m.p. 199° to 201°C. dec.

Workup

  1. temperatureunder reflux for 2.5 hours
  2. temperaturecooled
  3. additiontreated with 4 ml
  4. temperatureUpon cooling a solid separates
  5. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-35bba8b079914caab552999c317adeef
Source dataset
uspto-grants-1976_11
Patent number
US03991076

Reaction notes

Loading…