Morpholine → SUVN-G3031

HRID 1523404Notes

Reaction equation

HRID 1523404 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:13]2[CH2:18][CH2:17][N:16]([CH:19]3[CH2:22][CH2:21][CH2:20]3)[CH2:15][CH2:14]2)=[CH:8][CH:7]=1)=[O:4].[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:19]1([N:16]2[CH2:17][CH2:18][CH:13]([O:12][C:9]3[CH:10]=[CH:11][C:6]([NH:5][C:3](=[O:4])[CH2:2][N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:7][CH:8]=3)[CH2:14][CH2:15]2)[CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 682871802-Chloro-N-[4-[(1-cyclobutyl-4-piperidinyl)oxy]phenyl]acetamide

Product 1

HCID 60151477SUVN-G3031Yield 80.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-Chloro-N-[4-(1-cyclobutyl piperidin-4-yloxy)phenyl]acetamide (76.0 g, 0.236, obtained in above step), morpholine (30.8 g, 0.353 moles) and potassium carbonate (98 g, 0.71 moles) in acetonitrile (1.5 L) was stirred for 5 hours at reflux temperature. The mixture was partitioned between ethyl acetate (1 L) and water (1 L). The layers were separated, and the aqueous layer was extracted with ethyl acetate (2×500 mL). The combined organic layers were washed with water twice, dried over sodium sulfate and concentrated under vacuum. The crude compound was purified by flash chromatography using (methanol:chloroform, 2:8) to afford the title compound 71 g (Yield: 80%).

Workup

  1. temperatureat reflux temperature
  2. customThe mixture was partitioned between ethyl acetate (1 L) and water (1 L)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (2×500 mL)
  5. washThe combined organic layers were washed with water twice
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe crude compound was purified by flash chromatography

Sources & evidence

ORD record
ord-180cdb5f21674c0ca4175c064a483d0f
Source dataset
uspto-grants-2015_07
Patent number
US09079888B2

Reaction notes

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