Water → 1,2,3,9-tetrahydro-9-methyl-3-[[5-methyl(triphenylmethyl)-1H-imidazol-4-yl]methyl]carbazol-4-one

HRID 1590457Notes

Reaction equation

HRID 1590457 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][N:22]1[C:34]2[CH2:33][CH2:32][CH:31]([CH2:35][C:36]3[N:37]=[CH:38][NH:39][C:40]=3[CH3:41])[C:30](=[O:42])[C:29]=2[C:28]2[C:23]1=[CH:24][CH:25]=[CH:26][CH:27]=2.C(N(CC)CC)C.O>CN(C=O)C>[CH3:21][N:22]1[C:34]2[CH2:33][CH2:32][CH:31]([CH2:35][C:36]3[N:37]=[CH:38][N:39]([C:7]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)([C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)[C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[C:40]=3[CH3:41])[C:30](=[O:42])[C:29]=2[C:28]2[C:23]1=[CH:24][CH:25]=[CH:26][CH:27]=2

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 172316GR 67330

Product 1

HCID 142339301,2,3,9-tetrahydro-9-methyl-3-[[5-methyl(triphenylmethyl)-1H-imidazol-4-yl]methyl]carbazol-4-oneYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of triphenylchloromethane (286 mg) in dry DMF (10 ml) was added dropwise to a stirred solution of 1,2,3,9-tetrahydro-9-methyl-3-[(5-methyl-1H-imidazol-4-yl)methyl]-4H-carbazol-4-one (292 mg) and triethylamine (101 mg) in dry DMF (20 ml) and the resulting solution was stirred at room temperature under nitrogen for 3.5 h. The reaction mixture was then poured into water (100 ml) and the resultant suspension was extracted with dichloromethane (3×50 ml). The combined, dried organic extracts were adsorbed onto FCC silica which was then applied to a column and FCC eluting with System A (150:8:1) gave a solid which was further purified by crystallisation from dichloromethane:hexane (2:1) to give the title compound (304 mg), m.p. 193°-195°.

Workup

  1. extractionthe resultant suspension was extracted with dichloromethane (3×50 ml)
  2. washeluting with System A (150:8:1)
  3. customgave a solid which
  4. customwas further purified by crystallisation from dichloromethane:hexane (2:1)

Sources & evidence

ORD record
ord-823d75b325914c1f84e88477fdb97c3e
Source dataset
uspto-grants-1993_04
Patent number
US05202343

Reaction notes

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