Triethylamine → 1-Adamantan-1-yl-3-{3-[4-(3-chloro-phenyl)-piperazin-1-yl]-propyl}-urea; dihydrochloride

HRID 1639161Notes

Reaction equation

HRID 1639161 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][CH2:43][NH2:44])[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][CH2:43][NH:44][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 35067593-[4-(3-Chlorophenyl)piperazin-1-yl]propan-1-amine

Product 1

HCID 117969151-Adamantan-1-yl-3-{3-[4-(3-chloro-phenyl)-piperazin-1-yl]-propyl}-urea; dihydrochloride

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 3-[4-(3-chlorophenyl)-1-piperazinyl]propylamine (1.35 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 20% methanol in ethyl acetate solvent system, Rf=0.42) was isolated by gravity chromatography on silica gel and recrystallized from methylene chloride/hexane (1.52 gm, 61% of theory), mp.=174°-175° 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-e8f3a0ab64e94c7689b09a1210c3df1d
Source dataset
uspto-grants-1989_11
Patent number
US04882432

Reaction notes

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