Triethylamine → HCID 86734314, compound

HRID 1973838Notes

Reaction equation

HRID 1973838 reaction equation
[C:1](Cl)(=[O:10])[O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:19]1([NH:25][C:26]2([C:32]([O:34][CH3:35])=[O:33])[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>ClC(Cl)Cl>[C:19]1([NH:25][C:26]2([C:32]([O:34][CH3:35])=[O:33])[CH2:27][CH2:28][N:29]([C:1]([O:2][CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)=[O:10])[CH2:30][CH2:31]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 122981714-Piperidinecarboxylic acid, 4-(phenylamino)-, methyl ester

Product 1

HCID 86734314HCID 86734314, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 3.7 parts of (phenylmethyl) carbonochloridate and 2.1 parts of N,N-diethylethanamine in 75 parts of trichloromethane is added dropwise a solution of 4.6 parts of methyl 4-(phenylamino)-4-piperidinecarboxylate in 30 parts of trichloromethane (exothermic reaction: cooling with ice-water is necessary to keep the temperature below 25° C). Upon completion, stirring is continued for 5 hours at room temperature. The reaction mixture is washed twice with water, dried filtered and evaporated. The residue is purified by column-chromatography over silica gel using trichloromethane as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 2-propanol, yielding 4.2 parts of O4 -methyl O1 -(phenylmethyl) 4-(phenylamino)-1,4-piperidinedicarboxylate; mp. 105.8° C.

Workup

  1. customexothermic reaction
  2. customthe temperature below 25° C
  3. washThe reaction mixture is washed twice with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by column-chromatography over silica gel
  8. customThe pure fractions are collected
  9. customthe eluent is evaporated
  10. customThe residue is crystallized from 2-propanol

Sources & evidence

ORD record
ord-571c699a4ec9489d8b27b5dbf58300a5
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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