Triethylamine → HCID 10572963, compound

HRID 1639159Notes

Reaction equation

HRID 1639159 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.ClC([O:23][C:24](Cl)(Cl)Cl)=O.[N:28]1[CH:33]=[CH:32][CH:31]=[N:30][C:29]=1[N:34]1[CH2:39][CH2:38][N:37]([CH2:40][CH2:41][CH2:42][NH2:43])[CH2:36][CH2:35]1>C(Cl)Cl>[N:28]1[CH:33]=[CH:32][CH:31]=[N:30][C:29]=1[N:34]1[CH2:39][CH2:38][N:37]([CH2:40][CH2:41][CH2:42][NH:43][C:24]([NH:12][C:2]23[CH2:9][CH:8]4[CH2:7][CH:6]([CH2:5][CH:4]([CH2:10]4)[CH2:3]2)[CH2:11]3)=[O:23])[CH2:36][CH2:35]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 64150Amantadine HydrochlorideHCID 107042273-(4-pyrimidin-2-ylpiperazin-1-yl)propan-1-amine

Product 1

HCID 10572963HCID 10572963, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred suspension of 1-adamantanamine hydrochloride (1.25 gm, 0.0067 mol) and triethylamine (2.7 gm, 0.027 mol) in 25 mol of dry methylene chloride under a dry nitrogen atmosphere was added, dropwise, trichloromethyl chloroformate (1.33 gm, 0.0033 mol). The resulting suspension was refluxed for three hours, and then a solution of 3-[4-(2-pyrimidyl)-1-piperazinyl]propylamine (1.44 gm, 0.0067 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 30% methanol in ethyl acetate solvent system, Rf=0.39) was isolated by gravity chromatography on silica gel and recrystallized from methylene chloride/hexane (1.76 gm, 60% of theory), mp.=172°-173° 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-698f22d69bd24b88bcfc30a792b4b27a
Source dataset
uspto-grants-1989_11
Patent number
US04882432

Reaction notes

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