Hydrochloric Acid → HCID 23346248, compound

HRID 1856201Notes

Reaction equation

HRID 1856201 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH:14]=2)=[CH:4][CH:3]=1.Cl[CH2:16][CH2:17][CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)=[O:20].C(=O)([O-])[O-].[K+].[K+].Cl>C1C=CC=CC=1>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[CH2:14][CH2:13][N:12]([CH2:16][CH2:17][CH2:18][C:19]([C:21]3[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=3)=[O:20])[CH2:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 23346259HCID 23346259, compound

Product 1

HCID 23346248HCID 23346248, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
98 °C

Procedure

A mixture of 11.2 g of 4-[(4-chlorophenyl)thio]-1,2,3,6-tetrahydropyridine, 10.0 g of 4-chloro-p-fluorobutyrophenone and 6.9 g of potassium carbonate is heated at 98° C. for 1 hour. The mixture is taken up in benzene and filtered. Evaporation of the filtrate gives a brown oil which is treated with a large excess of 1 N hydrochloric acid. The resulting precipitate is collected to afford 8.9 g (46%) of tan powder, m.p. 208°-210° C. Recrystallization from acetonitrile yields off-white crystals, m.p. 220°-222° C.

Workup

  1. filtrationfiltered
  2. customEvaporation of the filtrate
  3. customgives a brown oil which
  4. customThe resulting precipitate is collected

Sources & evidence

ORD record
ord-6f41519c8e9143268dd02c3a215ee584
Source dataset
uspto-grants-1980_08
Patent number
US04218455

Reaction notes

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