Norchlorcyclizine → HCID 21478657, compound

HRID 2292511Notes

Reaction equation

HRID 2292511 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[NH:9][C:8](=[O:16])[CH2:7][C:6]1=[O:17].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([CH:25]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:26]2[CH2:27][CH2:28][N:29]([CH2:2][CH2:3][CH2:4][N:5]3[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[NH:9][C:8](=[O:16])[CH2:7][C:6]3=[O:17])[CH2:30][CH2:31]2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 9340Norchlorcyclizine2×HCID 11430Potassium CarbonateHCID 21478575HCID 21478575, compound

Product 1

HCID 21478657HCID 21478657, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Twenty five milliliters of dimethylformamide is added to 2.3 g of the compound of Example 209, 2.6 g of 1-[(4-chlorophenyl)phenylmethyl]piperazine and 2.2g of potassium carbonate and the resulting mixture is stirred at 100° C. for 4 hours. To the mixture, 0.35 g of 1-[(4-chlorophenyl)phenylmethyl]piperazine is added and the resulting mixture is stirred at 100° C. for 2.5 hours. The precipitate is removed by filtration and the filtrate is condensed, followed by purification by silica gel column chromatography (ethyl acetate:methanol=9:1-8:1) to obtain 3.7 g of (210).

Workup

  1. stirringthe resulting mixture is stirred at 100° C. for 2.5 hours
  2. customThe precipitate is removed by filtration
  3. customcondensed
  4. customfollowed by purification by silica gel column chromatography (ethyl acetate:methanol=9:1-8:1)

Sources & evidence

ORD record
ord-5ef974d31ae54cc19378f279f79fc94a
Source dataset
uspto-grants-1997_11
Patent number
US05683998

Reaction notes

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