Sodium Hydroxide → HCID 58551177, compound

HRID 1908022Notes

Reaction equation

HRID 1908022 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][C:4]=1[C:12]([F:15])([F:14])[F:13].[OH-].[Na+].Cl.[NH:19]1[CH2:24][CH2:23][C:22](O)([OH:25])[CH2:21][CH2:20]1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([N:19]2[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]2)=[O:8])=[CH:5][C:4]=1[C:12]([F:15])([F:14])[F:13]

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 27752984-Methoxy-3-(trifluoromethyl)benzoyl chlorideHCID 116368364,4-Piperidinediol, hydrochloride

Product 1

HCID 58551177HCID 58551177, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 4-methoxy-3-(trifluoromethyl)benzoyl chloride (4.00 g, 16.8 mmol) in toluene (16 mL) and a solution of NaOH (3.8 mL of 4.0 M, 15 mmol) were contemporaneously added drop-wise to a solution of piperidine-4,4-diol hydrochloride (2.30 g, 15.2 mmol) in NaOH (7.6 mL of 2.0 M, 15 mmol) at 25° C. The mixture was stirred for 90 min before the toluene was removed in vacuo. The alkaline phase was extracted with dichloromethane (3 times). The organics were combined, washed with brine, dried over Na2SO4, and concentrated in vacuo to provide 1-(4-methoxy-3-(trifluoromethyl)benzoyl)piperidin-4-one (4.2 g, 91%). ESI-MS m/z calc. 301.3. found 302.2 (M+1)+. Retention time: 0.95 minutes (3 min run). 1H NMR (400 MHz, CDCl3) δ 7.77 (d, J=1.9 Hz, 1H), 7.70 (dd, J=8.6, 2.1 Hz, 1H), 7.09 (d, J=8.6 Hz, 1H), 3.98 (s, 3H), 3.94 (s, 4H), 2.55 (s, 4H).

Workup

  1. customat 25° C
  2. customwas removed in vacuo
  3. extractionThe alkaline phase was extracted with dichloromethane (3 times)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5fa91f7ea52641e1bc4e8e5e24ac2342
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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