Triethylamine → HCID 9888180, compound

HRID 1639158Notes

Reaction equation

HRID 1639158 reaction equation
Cl.[C:2]12([NH2:12])[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2.C(N(CC)CC)C.Cl[C:21](OC(Cl)(Cl)Cl)=[O:22].[Cl:28][C:29]1[CH:30]=[C:31]([N:35]2[CH2:40][CH2:39][N:38]([CH2:41][CH2:42][NH2:43])[CH2:37][CH2:36]2)[CH:32]=[CH:33][CH:34]=1>C(Cl)Cl>[Cl:28][C:29]1[CH:30]=[C:31]([N:35]2[CH2:36][CH2:37][N:38]([CH2:41][CH2:42][NH:43][C:21]([NH:12][C:2]34[CH2:9][CH:8]5[CH2:7][CH:6]([CH2:5][CH:4]([CH2:10]5)[CH2:3]3)[CH2:11]4)=[O:22])[CH2:39][CH2:40]2)[CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 64150Amantadine HydrochlorideHCID 127267362-(4-(3-Chlorophenyl)piperazin-1-yl)ethan-1-amine

Product 1

HCID 9888180HCID 9888180, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred suspension of 1-adamantanamine hydrochloride (1.0 gm, 0.0053 mol) and triethylamine (2.2 gm, 0.021 mol) in 25 ml of dry methylene chloride under a dry nitrogen atmosphere was added, dropwise, trichloromethyl chloroformate (1.15 gm, 0.0027 mol). The resulting suspension was refluxed for three hours, and then a solution of 2-[4-(3-chlorophenyl)-1-piperazinyl]ethylamine (1.28 gm, 0.0053 mol) in 15 ml of dry methylene chloride was added. The resulting mixture was allowed to stir at room temperature overnight. The reaction mixture was then diluted to 200 ml with methylene chloride, washed with 3% aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated on a rotary evaporator. The title compound (TLC on silica gel using a 5% methanol in ethyl acetate solvent system, Rf=0.43) was isolated by preparatory high pressure liquid chromatography (HPLC) on silica gel (using a gradient consisting of from 10% ethyl acetate in hexane to 20% methanol in ethyl acetate) and recrystallized from methylene chloride/hexane (1.51 gm, 68% of theory), mp.=136°-137° C.

Workup

  1. additionwas added
  2. temperatureThe resulting suspension was refluxed for three hours
  3. washwashed with 3% aqueous sodium bicarbonate solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-2ee1c14aa7dc4b6b9d2ef7d78378f22e
Source dataset
uspto-grants-1989_11
Patent number
US04882432

Reaction notes

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