Toluene → HCID 57791776, compound

HRID 1091786Notes

Reaction equation

HRID 1091786 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.Cl[CH2:16][C:17]([N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:18].C1(C)C=CC=CC=1.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[O:18]=[C:17]([N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)[CH2:16][O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 884401-(Chloroacetyl)pyrrolidineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 57791776HCID 57791776, compoundYield 116%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

Tert-butyl 4-hydroxypiperidine-1-carboxylate (4 g, 19.87 mmol), tetrabutylammonium hydrogensulfate (0.337 g, 0.99 mmol) and 2-chloro-1-pyrrolidin-1-yl-ethanone (3.87 g, 25.84 mmol) were added to toluene (50 mL) to this was added NaOH (19.87 g, 198.75 mmol) in water (20 ml) and the reaction was stirred at 25° C. overnight. The reaction mixture was quenched with water (100 mL), extracted with Et2O (3×75 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford the desired material as an orange liquid (7.20 g, >100% yield); 1H NMR (400.13 MHz, DMSO-d6) δ 1.40 (9H, s), 1.86 (8H, m), 3.02 (4H, s), 3.38 (2H, t), 3.54 (1H, m), 3.60 (2H, m), 4.07 (2H, s).

Workup

  1. customThe reaction mixture was quenched with water (100 mL)
  2. extractionextracted with Et2O (3×75 mL)
  3. dry with materialthe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-89942252c8844361a9c4e98616cf23d1
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

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