Ethyl Acetate → HCID 178482768, compound

HRID 2209821Notes

Reaction equation

HRID 2209821 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].C1(N=C=NC2CCCCC2)CCCCC1.[OH:28][CH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([C@H:38]2[CH2:43][CH2:42][C@H:41]([NH:44][CH3:45])[CH2:40][CH2:39]2)=[C:34]([CH2:46][NH:47][CH3:48])[CH:33]=1.C(OCC)(=O)C>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:44]([C@H:41]2[CH2:40][CH2:39][C@H:38]([C:35]3[CH:36]=[CH:37][C:32]([CH2:31][CH2:30][CH2:29][OH:28])=[CH:33][C:34]=3[CH2:46][NH:47][CH3:48])[CH2:43][CH2:42]2)[CH3:45])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10868DicyclohexylcarbodiimideHCID 798743,4-Dichlorophenylacetic acidHCID 178482764HCID 178482764, compound

Product 1

HCID 178482768HCID 178482768, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
50 °C

Procedure

141 mg (0.68 mMol) of 3,4-dichlorophenylacetic acid in 5 ml of xylene are mixed with 112 mg (0.54 mMol) of N,N'-dicyclohexylcarbodiimide and heated to 50° C. for 1 hour. After the addition of 200 mg (0.68 mMol) of trans-4-[4-(3-hydroxypropyl)methylaminomethylphenyl]-N-methylcyclohexylamine the mixture is stirred overnight at 140° C. After cooling to ambient temperature and adding ethyl acetate, the mixture is washed with water and saturated saline solution, then dried and evaporated down. After purification by column chromatography (alumina, ethyl acetate/methanol=100:1 to 10:1, v:v), 110 mg (34% of theory) of the title compound are obtained, melting point 82°-84° C.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. washthe mixture is washed with water and saturated saline solution
  3. customdried
  4. customevaporated down
  5. customAfter purification by column chromatography (alumina, ethyl acetate/methanol=100:1 to 10:1, v:v), 110 mg (34% of theory) of the title compound
  6. customare obtained

Sources & evidence

ORD record
ord-5d1adb2cd5ab471099fb67e00436a6c8
Source dataset
uspto-grants-1995_10
Patent number
US05455273

Reaction notes

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