Pyrrolidine → HCID 71502739, compound

HRID 1627602Notes

Reaction equation

HRID 1627602 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[C:17]([CH3:23])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO[CH:26](OC)[N:27]([CH3:29])[CH3:28].N1CC[CH2:34][CH2:33]1>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[C:17](/[CH:23]=[CH:29]/[N:27]3[CH2:26][CH2:34][CH2:33][CH2:28]3)[CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 31268PyrrolidineHCID 78373Dimethylformamide dimethyl acetalHCID 44128630HCID 44128630, compound

Product 1

HCID 71502739HCID 71502739, compoundYield 83%

Conditions

Temperature
120 °C

Procedure

47.3 g (0.15 mol) 4-(4-Cyano-3-methyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester, 43.8 mL (0.33 mol) N,N-dimethylformamide dimethylacetal and 81.9 mL pyrrolidine (0.99 mol) were mixed and the mixture was heated within 30 min to 90° C. and kept at this temperature for 2 h. All volatile content was allowed to distil off. The temperature was raised to 120° C. and kept at this temperature for 27 h. Heating was discontinued and the dark highly viscous residue was dissolved in 400 mL MTB ether, washed twice with 200 mL saturated aqueous NaHCO3 and once with 200 mL water. The organic layer was concentrated and recrystallised from isopropanol/water (245 mL/105 mL) collected and dried to yield 49.5 g (yield 83%, purity 96.4%) of 4-[4-Cyano-3-((E)-2-pyrrolidin-1-yl-vinyl)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester

Workup

  1. temperaturethe mixture was heated within 30 min to 90° C.
  2. customto distil off
  3. waitkept at this temperature for 27 h
  4. temperatureHeating
  5. dissolutionthe dark highly viscous residue was dissolved in 400 mL MTB ether
  6. washwashed twice with 200 mL saturated aqueous NaHCO3 and once with 200 mL water
  7. concentrationThe organic layer was concentrated
  8. customrecrystallised from isopropanol/water (245 mL/105 mL)
  9. customcollected
  10. customdried

Sources & evidence

ORD record
ord-f7bf80963dbd400fbcf35a53c0286452
Source dataset
uspto-grants-2014_07
Patent number
US08785642B2

Reaction notes

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