HCID 13061531, compound → HCID 13061551, compound

HRID 1447810Notes

Reaction equation

HRID 1447810 reaction equation
C1(O[C:8](=[O:27])[CH:9]([C:11]2([OH:26])[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])[CH2:13][CH2:12]2)[CH3:10])C=CC=CC=1>C(N)CCC>[Cl:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][CH2:17][N:14]1[CH2:13][CH2:12][C:11]([CH:9]([CH3:10])[C:8]([NH:14][CH2:13][CH2:12][CH2:11][CH3:9])=[O:27])([OH:26])[CH2:16][CH2:15]1

Participants

3

Reactant 1

HCID 13061531HCID 13061531, compound

Product 1

HCID 13061551HCID 13061551, compound

Reagents, catalysts & solvents 1

HCID 8007ButylamineSolvent

Procedure

A solution of 5 g of 2-(1-o-chlorophenethyl-4-hydroxy-4-piperidyl)propionic acid phenyl ester and 50 cc of n-butylamine is boiled at reflux for 18 hours in an atmosphere of nitrogen. The excess n-butylamine is then removed by evaporation at reduced pressure, the residue is taken up in chloroform and the organic phase is washed twice with water and dried over magnesium sulphate. The chloroform is evaporated at reduced pressure. The residue is treated with maleic acid in acetone and the title compound is crystallized from acetone/ether (M.P. of hydrogen maleate 130°-133° C.).

Workup

  1. temperatureat reflux for 18 hours in an atmosphere of nitrogen
  2. customThe excess n-butylamine is then removed by evaporation at reduced pressure
  3. washthe organic phase is washed twice with water
  4. dry with materialdried over magnesium sulphate
  5. customThe chloroform is evaporated at reduced pressure
  6. additionThe residue is treated with maleic acid in acetone
  7. customthe title compound is crystallized from acetone/ether (M.P. of hydrogen maleate 130°-133° C.)

Sources & evidence

ORD record
ord-f6ce8e492ff243abbbc5e8ab584ebb51
Source dataset
uspto-grants-1979_12
Patent number
US04178377

Reaction notes

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