Sodium Hydroxide → HCID 18700415, compound

HRID 2288955Notes

Reaction equation

HRID 2288955 reaction equation
[C:1]1([C:7]2[O:11][C:10]([CH:12]3[CH2:17][CH2:16][N:15](C(=O)C)[CH2:14][CH2:13]3)=[N:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO.O>[C:1]1([C:7]2[O:11][C:10]([CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)=[N:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18700447HCID 18700447, compound

Product 1

HCID 18700415HCID 18700415, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 1-[4-(5-phenyl-oxazol-2-yl)-piperidin-1-yl]-ethanone (30.0 g, 110.99 mmol), prepared as part B, in MeOH (450 ml) is treated with a solution of NaOH (44.40 g, 1109.90 mmol) in water (150 ml), heated at 75° C. for 18 hours, and then the reaction mixture is concentrated to 1/3 volume. Upon addition of ca. an equal volume of water, crystallization occurred. The solids are filtered, washed with water and dried in a vacuum over at 70° C. to afford 4-(5-phenyl-oxazol-2yl)-piperidine as a white solid. 1HNMR (CDCl3): d 7.61 (d, 2H, J=7.4 Hz), 7.40 (t, 2H, J=7.4 Hz), 7.30 (t, 1H, J=7.4 Hz), 7.23 (s, 1H), 3.19 (d t, 2H, J=11.8, 3.3 hz), 2.99 (t t, 1H, J=11.8 3.9 Hz), 2.76 (m, 2H), 2.10 (m, 2H), 1.82 (m, 2H).

Workup

  1. concentrationthe reaction mixture is concentrated to 1/3 volume
  2. additionUpon addition
  3. customan equal volume of water, crystallization
  4. filtrationThe solids are filtered
  5. washwashed with water
  6. customdried in a vacuum over at 70° C.

Sources & evidence

ORD record
ord-141c4084975f43b19cd64f6b6e8a818e
Source dataset
uspto-grants-2000_07
Patent number
US06090825

Reaction notes

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