Hydrochloric Acid → HCID 21108374, compound

HRID 1766029Notes

Reaction equation

HRID 1766029 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:33])[CH2:15][CH2:16][CH:17]([C:19]3[CH:32]=[CH:31][C:22]4[CH2:23][CH2:24][N:25]([CH:28]([CH3:30])[CH3:29])[CH2:26][CH2:27][C:21]=4[CH:20]=3)O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][CH2:10][N:11]([C:14](=[O:33])[CH2:15]/[CH:16]=[CH:17]/[C:19]3[CH:32]=[CH:31][C:22]4[CH2:23][CH2:24][N:25]([CH:28]([CH3:30])[CH3:29])[CH2:26][CH2:27][C:21]=4[CH:20]=3)[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 521998p-Toluenesulfonic acid monohydrateHCID 21108270HCID 21108270, compound

Product 1

HCID 21108374HCID 21108374, compoundYield 54.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 4-[4-(4-chlorophenyl)-1-piperidinyl]-1-(3-isopropyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-4-oxo-1-butanol (0.14 g, 0.30 mmol) obtained in Example 212 and p-toluenesulfonic acid monohydrate (0.03 g, 0.16 mmol) in toluene (10 mL) was refluxed for 24 hours under heating. The reaction solution was concentrated under reduced pressure, and the resultant residues were purified by alumina column chromatography (developing solvent; hexane:ethyl acetate=1:1), whereby 0.09 g free base of the title compound was obtained as colorless amorphous powder. The resultant powder was dissolved in ethyl acetate and treated with 4 N hydrochloric acid in ethyl acetate under cooling with ice-bath, whereby 0.04 g of the title compound was obtained as colorless amorphous powder.

Workup

  1. temperatureunder heating
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customthe resultant residues were purified by alumina column chromatography (developing solvent; hexane:ethyl acetate=1:1), whereby 0.09 g free base of the title compound
  4. customwas obtained as colorless amorphous powder
  5. temperatureunder cooling with ice-bath

Sources & evidence

ORD record
ord-cb682bf7276f42a4a1f4a7a656ce3bcd
Source dataset
uspto-grants-2007_06
Patent number
US07229986B2

Reaction notes

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