Ethanol → HCID 13336364, compound

HRID 986287Notes

Reaction equation

HRID 986287 reaction equation
[CH2:1]([N:3]([CH2:22][CH2:23][CH2:24][CH:25]1[CH2:30][CH2:29][N:28](CC2C=CC=CC=2)[CH2:27][CH2:26]1)[C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:7]=1)=[O:5])[CH3:2].ClC(OCC(Cl)(Cl)Cl)=O.[OH-].[K+].C(O)C>C1(C)C=CC=CC=1>[C:15]1([CH3:6])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1.[CH2:1]([NH:3][CH2:4][CH3:6])[CH3:2].[CH2:1]([N:3]([CH2:22][CH2:23][CH2:24][CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)[C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:7]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 870632,2,2-Trichloroethyl chloroformateHCID 20158360HCID 20158360, compound

Product 2

HCID 13336364HCID 13336364, compoundYield 174.9%HCID 22289835HCID 22289835, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Debenzylation is carried out as in Example 48, using N-ethyl-N-[3-(1-benzylpiperidin-4-yl)-propyl]-2-phenylquinoline-4-carboxamide (21 g) in toluene (400 ml), 2,2,2-trichloroethyl chloroformate (9 g), and then a 6N aqueous solution of potassium hydroxide (245 ml) and ethanol (550 ml), as the starting materials. After chromatography of the residue on silica gel using a toluene/diethylamine mixture (9/1) as the eluant, N-ethyl-N-[3-(piperidin-4-yl)-propyl]-2-phenylquinoline-4-carboxamide (10 g) is isolated; this is converted to its methanesulphonate in ethanol by the addition of an ethanolic solution of methanesulphonic acid. The methanesulphonate melts at 164° C.

Sources & evidence

ORD record
ord-167322eb04ce4970bb1792a93c06a07e
Source dataset
uspto-grants-1987_12
Patent number
US04711890

Reaction notes

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