Water → HCID 67861498, compound

HRID 249053Notes

Reaction equation

HRID 249053 reaction equation
F[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[OH:12][CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.O>CN1CCCC1=O>[CH3:9][O:8][C:6]([C:5]1[CH:10]=[CH:11][C:2]([N:18]2[CH2:19][CH2:20][CH:15]([CH2:14][CH2:13][OH:12])[CH2:16][CH2:17]2)=[CH:3][CH:4]=1)=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 67878Methyl 4-fluorobenzoateHCID 739534-Piperidineethanol

Product 1

HCID 67861498HCID 67861498, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 9.84 grams of methyl 4-fluorobenzoate (63.9 mmol) and 12.40 grams of 4-(2-hydroxyethyl)piperdine (96 mmol) in 50 mL N-methylpyrrolidin-2-one was heated to 110°-120° C. and stirred for 72 hours. The dark solution was cooled and poured into 400 mL water. The tan precipitate was filtered off and washed well with water to yield 11.89 grams of crude product as a tan powder (71%). The crude material was recrystallized once from 100 mL ethanol which gave 4.75 grams (40% recovery) of a tan powder. Melting point 110°-115° C. 2H NMR δ (acetone-d6): 1.27 (2H, quad of doub, J=3.8 hz & 12.2 hz); 1.47 (2H, quad, J=6.6 hz); 1.71 (1H, mult); 1.80 (2H, br doub); 2.83 (2H, trip of doub, J=2.5 hz & 12.6 hz); 3.62 (2H, trip, J=6.6 hz); 3.78 (3H, s); 3.92 (2H, br doub); 6.93 (2H, doub); 7.81 (2H, doub). 13C NMR δ (acetone-d6): 32.59, 33.36, 40.30, 48.61, 51.55, 59.81, 114.30, 119.26, 132.0, 155.29, 167.18.

Workup

  1. temperatureThe dark solution was cooled
  2. filtrationThe tan precipitate was filtered off
  3. washwashed well with water

Sources & evidence

ORD record
ord-5ec13bf206f347ef9b8a7a990c151e6b
Source dataset
uspto-grants-1993_05
Patent number
US05212269

Reaction notes

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