Methyl Ethyl Ketone → HCID 21486936, compound

HRID 1414284Notes

Reaction equation

HRID 1414284 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([N:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][C:11]([O:19][CH3:20])=[C:12]([O:17][CH3:18])[CH:13]=2)[CH:8]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:6].[NH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.CC(=O)CC>C(=O)(O)[O-].[K+].C(Cl)Cl>[CH3:18][O:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][C:11]=1[O:19][CH3:20])[CH:8]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[N:7]([C:5]([NH:4][CH2:3][CH2:2][N:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:6])[CH2:16][CH2:15]2

Participants

6

Reactant 3

HCID 6569Methyl Ethyl KetoneHCID 8082PiperidineHCID 21487009N-(2-chloroethyl)-6,7-dimethoxy-1-phenyl-3,4-dihydro-2(1H)-isoquinolinecarboxamide

Product 1

HCID 21486936HCID 21486936, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516893Potassium BicarbonateSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 3.0 parts of the N-(2-chloroethyl)-6,7-dimethoxy-1-phenyl-3,4-dihydro-2(1H)-isoquinolinecarboxamide prepared in Example 8 and 4.3 parts of piperidine in approximately 40 parts of 2-butanone is heated at 65°C. for 20 hours. The reaction mixture is then stripped in vacuo and the residue taken up in dilute aqueous potassium bicarbonate solution and methylene chloride. The organic layer is dried and stripped in vacuo and the residue is crystallized from ether to afford 6,7-dimethoxy-1-phenyl-N-(2-piperidinoethyl)-3,4-dihydro-2(1H)-isoquinolinecarboxamide, melting at about 101°-102°C.

Workup

  1. customThe organic layer is dried
  2. customthe residue is crystallized from ether

Sources & evidence

ORD record
ord-d2e5ae05b0d14b81a1e414fa744f035e
Source dataset
uspto-grants-1977_01
Patent number
US04001244

Reaction notes

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