Hydrochloric Acid → HCID 20357519, compound

HRID 2083773Notes

Reaction equation

HRID 2083773 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[C:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:4]=2[CH:3]=1.Br[CH2:23][CH2:24][CH2:25][OH:26].[I-].[K+].Cl>O.CN(C)C=O>[ClH:1].[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[C:16]3[CH2:21][CH2:20][N:19]([CH2:23][CH2:24][CH2:25][OH:26])[CH2:18][CH2:17]3)[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 123083-Bromo-1-propanolHCID 20357485HCID 20357485, compound

Product 1

HCID 20357519HCID 20357519, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3.5 g. (11.8 mmol) of 4-(2-chloro-9-xanthenylidene)piperidine (prepared as in Example 14), 2.0 g. (13.4 mmol) of 3-bromo-1-propanol and 50 mg. of potassium iodide in 50 ml. of dimethylformamide is stirred at 23° C. for 18 hours and 100° C. for 12 hours. The reaction mixture is poured into water, basified and extracted with a mixture of ether and ethyl acetate. The extract is washed with water, dried and the solvent evaporated. The residue is chromatographed on an alumina column using ethyl acetate-ether 1:1 as the eluent. The first fraction yields the product which is treated with ethereal hydrogen chloride to give 4-(2-chloro-9-xanthenylidene)-1-(3-hydroxypropyl)piperidine hydrochloride, m.p. 225°-258° C.

Workup

  1. extractionextracted with a mixture of ether and ethyl acetate
  2. washThe extract is washed with water
  3. customdried
  4. customthe solvent evaporated
  5. customThe residue is chromatographed on an alumina column
  6. customThe first fraction yields the product which

Sources & evidence

ORD record
ord-a082273531984202b65defff9c8cdb10
Source dataset
uspto-grants-1978_04
Patent number
US04086350

Reaction notes

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