Morpholine → HCID 59837379, compound

HRID 272997Notes

Reaction equation

HRID 272997 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([CH2:18][N:19]([CH3:21])[CH3:20])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:20][N:19]([CH3:21])[CH2:18][C:12]1([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:7][CH:8]=2)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 8083Morpholine2×HCID 11430Potassium Carbonate2×HCID 68576119HCID 68576119, compound

Product 1

HCID 59837379HCID 59837379, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-{4-[4-(3-chloropropoxy)phenyl]tetrahydro-2H-pyran-4-yl}-N,N-dimethylmethanamine (100 mg, 0.32 mmol), morpholine (100 mg, 1.1 mmol) and potassium carbonate (100 mg, 0.72 mmol) was heated at reflux in acetonitrile (5 ml) for 8 hours. Further morpholine (100 mg, 1.1 mmol) and potassium carbonate (100 mg, 0.72 mmol) were added and the reaction mixture heated at reflux for 6 hours. The reaction mixture was concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (90:10:1 by volume) to provide the title compound (61 mg, 52%). 1H NMR (400 MHz, CD3OD) δ 0.81-0.87 (m, 2H), 1.04-2.01 (m, 8H), 2.13-2.18 (m, 2H), 2.48-2.50 (m, 6H), 2.56 (t, 2H), 3.50 (t, 2H), 3.68-3.77 (m, 6H), 4.03 (t, 2H), 6.90 (d, 2H), 7.27 (d, 2H). HRMS ESI+ m/z 363.2635 [MH]+.

Workup

  1. temperaturewas heated
  2. temperaturethe reaction mixture heated
  3. temperatureat reflux for 6 hours
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (90:10:1 by volume)

Sources & evidence

ORD record
ord-c1b3473dd06642e2aa90af9f6d26a3b6
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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