Norchlorcyclizine → HCID 22161647, compound

HRID 1088693Notes

Reaction equation

HRID 1088693 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH:9]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[N:7]2[CH:21]=[N:22][C:23]([C:24]#[N:25])=[C:6]12)=[O:4].[Cl:26][C:27]1[CH:45]=[CH:44][C:30]([CH:31]([N:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:29][CH:28]=1.CN(C)C1C2C(=CC=CC=2N(C)C)C=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:26][C:27]1[CH:28]=[CH:29][C:30]([CH:31]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:38]2[CH2:39][CH2:40][N:41]([CH2:2][C:3]([N:5]3[CH2:10][CH:9]=[C:8]([C:11]4[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:18])[F:19])[CH:12]=4)[N:7]4[CH:21]=[N:22][C:23]([C:24]#[N:25])=[C:6]34)=[O:4])[CH2:42][CH2:43]2)=[CH:44][CH:45]=1

Participants

6

Reactant 3

HCID 9340NorchlorcyclizineHCID 88675Proton sponge2×HCID 15712537HCID 15712537, compound

Product 1

HCID 22161647HCID 22161647, compoundYield 77.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.53 g of 1-(chloroacetyl)-1,2-dihydro-4-[3-(trifluoromethyl)phenyl]imidazo[1,5-a]pyrimidine-8-carbonitrile, 1.32 g of N-(p-chlorobenzhydryl)piperazine and 990 mg of [1,8-bis(dimethylamino)naphthalene, N,N,N',N'-tetramethyl-1,8-naphthalenediamine] in 60 ml of toluene was stirred and heated at reflux for 17 hours. The reaction mixture was filtered hot. The filtrate was cooled, then shaken with 50.0 ml of 1N sodium hydroxide and worked up by the procedure of Example 7 to obtain a viscous oil. The oil in ethyl acetate was passed through a silica column to give a solid upon evaporation of the solvent. The solid was dissolved in 40% ethyl acetate/hexane and again passed through a short silica column. Evaporation of the solvent in vacuo gave 2.00 g of the desired product as a yellow solid, mp 105°-107° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 17 hours
  3. filtrationThe reaction mixture was filtered hot
  4. temperatureThe filtrate was cooled
  5. stirringshaken with 50.0 ml of 1N sodium hydroxide
  6. customto obtain a viscous oil
  7. customto give a solid
  8. customupon evaporation of the solvent
  9. dissolutionThe solid was dissolved in 40% ethyl acetate/hexane
  10. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-1b0c450addc649d49e6d6d8e35ff37b2
Source dataset
uspto-grants-1990_10
Patent number
US04963552

Reaction notes

Loading…