Hydrochloric Acid → HCID 22285420, compound

HRID 1062456Notes

Reaction equation

HRID 1062456 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)[CH:10]=[C:11]([C:13]([N:15]2[CH2:20][CH2:19][C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(O)[CH2:17][CH2:16]2)=[O:14])[N:12]=1.Cl>ClCCl.CCOCC>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]([N:9]2[CH:10]=[C:11]([C:13]([N:15]3[CH2:16][CH:17]=[C:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:19][CH2:20]3)=[O:14])[N:12]=[C:8]2[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22285370HCID 22285370, compound

Product 1

HCID 22285420HCID 22285420, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A 30-mg sample of 1-{[2-(2-methylphenyl)-1-(4-chlorophenyl)-1H-imidazol-4-yl]carbonyl}-4-phenyl-4-piperidinol (Table entry 414), was dissolved in 20 mL dichloromethane, and then 5 mL 2M HCl in ether was added to the solution. Evaporation of the solvent at high temperature (ca. 70° C., 16 hr) in a multiple sample evaporator (GeneVac) gave 1-{[1-(4-chlorophenyl)-2-(2-methylphenyl)-1H-imidazol-4-yl]carbonyl}-4-phenyl-1,2,3,6-tetrahydropyridine (yellow solid). 1H NMR (400 MHz, CD3COCD3) δ 8.31 (s, 1H), 7.05-7.35 (m, 13 H), 6.05 (s, 1 H), 4.2 (m, 2 H), 3.85 (m, 2H), 2.5 (m, 2H), 2.0 (s, 3H); LC-MS m/z 454 (MH+), retention time 2.92 min (method 2).

Workup

  1. customEvaporation of the solvent at high temperature (ca. 70° C., 16 hr)
  2. customin a multiple sample evaporator (GeneVac)

Sources & evidence

ORD record
ord-7095ba47c21d45d99ab281f1ffea109b
Source dataset
uspto-grants-2005_11
Patent number
US06960601B2

Reaction notes

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