Ammonia → (+)-Cis-3-ethoxymethyl-4-(3,4-dichlorophenyl)-piperidine

HRID 227574Notes

Reaction equation

HRID 227574 reaction equation
Br.C[N:3]1[CH2:8][CH2:7][C@H:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=2)[C@H:5]([CH2:17][O:18][CH2:19][CH3:20])[CH2:4]1.ClC(OC(Cl)=O)C.[OH-].[Na+].N>CO.C(Cl)Cl>[CH2:19]([O:18][CH2:17][C@H:5]1[C@@H:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=2)[CH2:7][CH2:8][NH:3][CH2:4]1)[CH3:20]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 14798Sodium HydroxideHCID 5213051-Chloroethyl chloroformateHCID 68534666(+)-Cis-1-methyl-3-ethoxymethyl-4-(3,4-dichlorophenyl)-piperidine hydrobromide

Product 1

HCID 68529854(+)-Cis-3-ethoxymethyl-4-(3,4-dichlorophenyl)-piperidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (13) 0.70 g and 1-chloroethylchloroformate (2.5 ml) was stirred at 100° C. for 2 days where after 4 N NaOH (25 ml) was added. The mixture was stirred with reflux overnight. After cooling, the mixture was extracted with toluene. The organic phase was dried and evaporated to give an oil which was subjected to column chromatography (SiO2, methylene chloride, MeOH, ammonia 9:1:1%) to give the product as pale crystals. Mp 68-70° C.

Workup

  1. additionwas added
  2. temperaturewith reflux overnight
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with toluene
  5. customThe organic phase was dried
  6. customevaporated
  7. customto give an oil which

Sources & evidence

ORD record
ord-ab566e4a04094eceb16dc71208c357c4
Source dataset
uspto-grants-2009_07
Patent number
US07560562B2

Reaction notes

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