Diisopropylethylamine → HCID 24703350, compound

HRID 548620Notes

Reaction equation

HRID 548620 reaction equation
Cl.O.[NH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.CCN(C(C)C)C(C)C.[F:19][C:20]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:21]=1[C:22](Cl)=[O:23]>C(Cl)Cl>[F:19][C:20]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:21]=1[C:22]([N:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)=[O:23]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 874382,6-Difluorobenzoyl chlorideHCID 2723901Piperonylamine

Product 1

HCID 24703350HCID 24703350, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-piperidone monohydrate hydrochloride (1.0 g, 6.5 mmol) in methylene chloride (32 mL) at rt were successively added DIPEA (1.4 mL, 7.8 mmol) and 2,6-difluorobenzoyl chloride (0.82 mL, 6.5 mmol). The resulting heterogeneous mixture was stirred at rt for 2 d. The resulting mixture was washed with 1 N aq. sodium hydroxide (3×10 mL) and the combined basic aqueous portion was back-extracted with methylene chloride (2×10 mL). The organic extracts were combined and washed with 10% aq. citric acid (2×10 mL), brine (20 mL), and dried over anhyd sodium sulfate. Concentration under vacuum afforded the title compound a as a pale yellow solid (1.29 g, 83%). 1H NMR (400 MHz, d3-MeOD): δ 7.60 (m, 1H), 7.18-7.09 (m, 2H), 4.09 (t, J=6.4 Hz, 2H), 3.70 (t, J=6.3 Hz, 2H), 2.62 (t, J=6.4 Hz, 2H), 2.48 (t, J=6.3 Hz, 2H).

Workup

  1. customat rt
  2. washThe resulting mixture was washed with 1 N aq. sodium hydroxide (3×10 mL)
  3. extractionthe combined basic aqueous portion was back-extracted with methylene chloride (2×10 mL)
  4. washwashed with 10% aq. citric acid (2×10 mL), brine (20 mL)
  5. dry with materialdried over anhyd sodium sulfate
  6. concentrationConcentration under vacuum

Sources & evidence

ORD record
ord-d2ce66b91f6145b39e2cc0c1620d35fb
Source dataset
uspto-grants-2011_05
Patent number
US07943617B2

Reaction notes

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