Toluene → 1-(4-(1,4-Dioxaspiro[4.5]decan-8-yl)cyclohex-1-enyl)pyrrolidine

HRID 1257943Notes

Reaction equation

HRID 1257943 reaction equation
C1(C)C=CC=CC=1.[NH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1.[O:13]1[C:17]2([CH2:22][CH2:21][CH:20]([CH:23]3[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]3)[CH2:19][CH2:18]2)[O:16][CH2:15][CH2:14]1>O>[O:13]1[C:17]2([CH2:18][CH2:19][CH:20]([CH:23]3[CH2:28][CH2:27][C:26]([N:8]4[CH2:12][CH2:11][CH2:10][CH2:9]4)=[CH:25][CH2:24]3)[CH2:21][CH2:22]2)[O:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 31268PyrrolidineHCID 8109134-(1,4-Dioxa-spiro(4.5)dec-8-yl)-cyclohexanone

Product 1

HCID 679549881-(4-(1,4-Dioxaspiro[4.5]decan-8-yl)cyclohex-1-enyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Toluene (200 ml) and pyrrolidine (90 ml) were added to 4-(1,4-dioxaspiro[4.5]decan-8-yl)cyclohexanone (100 g) in a reaction vessel equipped with a Dean-Stark apparatus under an atmosphere of nitrogen. The mixture was refluxed for 3 hours while the water formed was removed by a Dean-Stark apparatus. After the reaction mixture had been cooled to a room temperature, it was washed with brine, and dried over anhydrous magnesium sulfate. The toluene was distilled off to give 1-(4-(1,4-dioxaspiro[4.5]decan-8-yl)cyclohex-1-enyl)pyrrolidine (105.8 g).

Workup

  1. customequipped with a Dean-Stark apparatus under an atmosphere of nitrogen
  2. customformed
  3. customwas removed by a Dean-Stark apparatus
  4. washit was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe toluene was distilled off

Sources & evidence

ORD record
ord-fb41a4f91529401aa114a48e63d90029
Source dataset
uspto-grants-2013_06
Patent number
US08465674B2

Reaction notes

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