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Allyl bromide → 2-Propenyl 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylate

HRID 1973788
Notes
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Reaction equation

HRID 1973788 reaction equation
[C:1]1([NH:7][C:8]2([C:22]([OH:24])=[O:23])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].CN(C)P(=O)(N(C)C)N(C)C.Br[CH2:38][CH:39]=[CH2:40]>O>[C:1]1([NH:7][C:8]2([C:22]([O:24][CH2:40][CH:39]=[CH2:38])=[O:23])[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:12][CH2:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 12679HexamethylphosphoramideHCID 6162334-Piperidinecarboxylic acid, 4-(phenylamino)-1-(2-phenylethyl)-HCID 5360545Sodium

Product 1

HCID 122981482-Propenyl 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
110 °C

Procedure

A mixture of 10.4 parts of 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylic acid, sodium salt and 75 parts of hexamethylphosphoric triamide is stirred and heated to 110° C for a while. After cooling to 20° C, 3.63 parts of 3-bromo-1-propene are added dropwise. Upon completion, stirring is continued for 20 hours at room temperature. The reaction mixture is poured onto 150 parts of water and the product is extracted with methylbenzene. The extract is washed with water, filtered and evaporated. The oily residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 5% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The oily residue is crystallized from hexane, yielding 2-propenyl 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylate; mp. 57.2° C.

Workup

  1. temperatureAfter cooling to 20° C
  2. stirringUpon completion, stirring
  3. extractionthe product is extracted with methylbenzene
  4. washThe extract is washed with water
  5. filtrationfiltered
  6. customevaporated
  7. customThe oily residue is purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and 5% of methanol as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated
  11. customThe oily residue is crystallized from hexane

Sources & evidence

ORD record
ord-039f306b59054020bfeff847c2e928e9
Source dataset
uspto-grants-1976_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03998834

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes