Methane → HCID 131717119, compound

HRID 1461332Notes

Reaction equation

HRID 1461332 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[C@H:13]([C:14]([O:16]CC)=[O:15])[CH2:12][CH2:11][N:10]([CH3:19])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.FC1C=C([C@H]2[C@@H](C(OCC)=[O:34])CCN(C)C2)C=CC=1.[OH-:39].[K+:40].CO.C>CC(O)C>[OH2:15].[OH2:34].[OH2:39].[OH2:15].[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[C@H:13]([C:14]([O-:16])=[O:15])[CH2:12][CH2:11][N:10]([CH3:19])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[K+:40]

Participants

6

Reactant 4

HCID 297MethaneHCID 887MethanolHCID 14797Potassium HydroxideHCID 131717121HCID 131717121, compound

Product 1

HCID 131717119HCID 131717119, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 26.53 parts of trans-ethyl 3-(3-fluorophenyl)-1-methyl-4-piperidinecarboxylate: cis-ethyl 3-(3-fluorophenyl)-1-methyl-4-piperidinecarboxylate (40:60), 6.52 parts of potassium hydroxide and 80 parts of methanol was stirred for 3 hours at reflux temperature. After the addition of 78 parts of 2-propanol, the reaction mixture was treated with charcoal. The whole was filtered and the filtrate was evaporated to near dryness in vacuo. The residue was treated with 7.2 parts of water and then diluted with ~210 parts of 1,1'-oxybisethane (to near cloud point). After cooling, the crystallized product was filtered off, washed with 1,1'-oxybisethane and recrystallized twice from a mixture of a minimal amount of damp 2-propanol and 1,1'-oxybisethane, yielding 26.1 parts (75%) of potassium (±)-trans-3-(3-fluorophenyl)-1-methyl-4-piperidinecarboxylate tetrahydrate; mp. 75.2° C. (interm. 1).

Workup

  1. temperatureat reflux temperature
  2. filtrationThe whole was filtered
  3. customthe filtrate was evaporated
  4. additionThe residue was treated with 7.2 parts of water
  5. additiondiluted with ~210 parts of 1,1'-oxybisethane (to near cloud point)
  6. temperatureAfter cooling
  7. filtrationthe crystallized product was filtered off
  8. washwashed with 1,1'-oxybisethane
  9. customrecrystallized twice from a mixture of a minimal amount of damp 2-propanol and 1,1'-oxybisethane

Sources & evidence

ORD record
ord-9c6e92384d5c4fa4b75fabb14a6bab9c
Source dataset
uspto-grants-1991_12
Patent number
US05075315

Reaction notes

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