Morpholine → HCID 9806658, compound

HRID 1369549Notes

Reaction equation

HRID 1369549 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:30]=[C:31](F)[CH:32]=1)[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:29])=[C:12]([NH:14][C:15](=[O:28])[C:16]2[CH:21]=[CH:20][C:19]([CH2:22][N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])=[CH:18][CH:17]=2)[CH:13]=1)=[O:6].[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>O>[F:1][C:2]1[CH:3]=[C:4]([CH:30]=[C:31]([N:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)[CH:32]=1)[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:29])=[C:12]([NH:14][C:15](=[O:28])[C:16]2[CH:17]=[CH:18][C:19]([CH2:22][N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])=[CH:20][CH:21]=2)[CH:13]=1)=[O:6]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 22291115HCID 22291115, compound

Product 1

HCID 9806658HCID 9806658, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-[5-(3,5-difluorobenzamido)-2-methylphenyl]-4-diethylaminomethylbenzamide (0.069 g) and morpholine (3 ml) was stirred and heated to 100° C. for 6 days. The mixture was cooled to ambient temperature and poured into water. The resultant solid was isolated, washed in turn with water and diethyl ether and dried under vacuum at 40° C. There was thus obtained the title compound (0.033 g); NMR Spectrum: (DMSOd6) 0.98 (t, 6H), 2.2 (s, 3H), 2.46-2.49 (m, 4H), 3.20-3.24 (m, 4H), 3.58 (s, 2H), 3.72-3.75 (m, 4H), 6.95 (d, 1H), 7.14 (d, 1H), 7.21 (d, 1H), 7.3 (s, 1H), 7.45 (s, 2H), 7.58 (d, 1H), 7.78 (s, 1H), 7.91 (d, 2H), 9.82 (s, 1H), 10.15 (s, 1H); Mass Spectrum: M+H+519.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customThe resultant solid was isolated
  3. washwashed in turn with water and diethyl ether
  4. customdried under vacuum at 40° C

Sources & evidence

ORD record
ord-90a927cc877b40bd9a0de79edcca4150
Source dataset
uspto-grants-2003_06
Patent number
US06579872B1

Reaction notes

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