Water → HCID 70578092, compound

HRID 1414569Notes

Reaction equation

HRID 1414569 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][C:5]2([C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:14][C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].C1O[C:30]([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)([CH2:31][CH2:32][CH2:33][Cl:34])[O:29]C1.O>C(O)CCC>[ClH:34].[F:41][C:38]1[CH:37]=[CH:36][C:35]([C:30]([CH2:31][CH2:32][CH2:33][N:2]2[CH2:3][CH2:4][C:5]3([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=4[O:14][C:15]4[C:20]3=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH2:6][CH2:7]2)=[O:29])=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27237782-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolaneHCID 70577204HCID 70577204, compound

Product 1

HCID 70578092HCID 70578092, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of xanthene-9-spiro-4'-piperidine hydrochloride (1 g.), potassium carbonate (1.2 g.) and γ-chloro-p-fluorobutyrophenone ethylene ketal (1.03 g.) in n-butanol is heated under reflux for 48 hours. The mixture is poured into water, extracted with ether, the ether solution evaporated and the residue warmed with 3N hydrochloric acid for 1 hour to hydrolyse the ketal. The acidic solution is extracted with ethyl acetate, the solvent evaporated and the residue recrystallised from ethyl acetate to give 1'-[3-(p-fluorobenzoyl)propyl]xanthene-9-spiro-4'-piperidine hydrochloride (0.51 g.), m.p. 219°-222° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 48 hours
  3. extractionextracted with ether
  4. customthe ether solution evaporated
  5. temperaturethe residue warmed with 3N hydrochloric acid for 1 hour
  6. extractionThe acidic solution is extracted with ethyl acetate
  7. customthe solvent evaporated
  8. customthe residue recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-79f312ba9f904589a802c0365629fcc8
Source dataset
uspto-grants-1977_01
Patent number
US04001419

Reaction notes

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