Triethylamine → 4-(9,10-Dihydro-10-methyl-9-acridinyl)-1-(2,2,2-trichloroethyloxycarbonyl)piperidine

HRID 36612

Reaction equation

HRID 36612 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])=[O:3].[CH3:10][N:11]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]([CH:25]2[CH2:30][CH2:29][N:28](C)[CH2:27][CH2:26]2)[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]1=2.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:10][N:11]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]([CH:25]2[CH2:30][CH2:29][N:28]([C:2]([O:4][CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])=[O:3])[CH2:27][CH2:26]2)[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]1=2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 870632,2,2-Trichloroethyl chloroformateHCID 141757999,10-Dihydro-10-methyl-9-(1-methyl-4-piperidinyl)acridine

Product 1

HCID 152894794-(9,10-Dihydro-10-methyl-9-acridinyl)-1-(2,2,2-trichloroethyloxycarbonyl)piperidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Trichloroethyl chloroformate (1.06 mL, 7.7 mmol) is added over a 10 minute period to a solution of 9,10-dihydro-10-methyl-9-(1-methyl-4-piperidinyl)acridine (453 mg, 1.55 mmol) [(Tetrahedron Letters, 29, 5701 (1988)] and triethylamine (649 μl, 4.65 mmol) in 20 mL of dry toluene at 85° C. The reaction is worked up after 30 minutes by extracting with EtOAc and washing with a 10% NaOH solution. The crude product is obtained after the solvent is removed.

Workup

  1. extractionby extracting with EtOAc
  2. washwashing with a 10% NaOH solution

Sources & evidence

ORD record
ord-9e0dd83f798f4dbe8b7f1a52e3c99f19
Source dataset
uspto-grants-1995_05
Patent number
US05416087

Linked notes

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