Morpholine, 4-(1-cyclohexen-1-yl)- → Diphenyl 1-morpholinocyclohexane-1-phosphonate

HRID 1380152Notes

Reaction equation

HRID 1380152 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]=2)[CH2:3][CH2:2]1.[P:13]([O-:28])([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2([P:13]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:28])[O:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 69589Morpholine, 4-(1-cyclohexen-1-yl)-HCID 23418553Diphenoxyphosphanolate

Product 1

HCID 13685034Diphenyl 1-morpholinocyclohexane-1-phosphonate

Procedure

To 1-morpholinocyclohexene (21.5 g; 0.13 mol) was added diphenyl phosphite (30 g; 0.13 mol) drop-wise during 20 minutes. The mixture which began to deposit a solid was heated at 100° for 30 minutes following the addition. After cooling, the resulting solid was recrystallized from benzene/hexane to yield pure diphenyl 1-morpholinocyclohexane-1-phosphonate, 37 g (70%), mp 103°-6°. NMR and IR spectra support the structure. Analysis: Calculated for C22H28NO4P; N, 3.49%; P, 7.73%. Found: N, 3.40% P, 7.70%. ##STR10##

Workup

  1. temperaturewas heated at 100° for 30 minutes
  2. additionthe addition
  3. temperatureAfter cooling
  4. customthe resulting solid was recrystallized from benzene/hexane

Sources & evidence

ORD record
ord-db1166212d0a49488f561218a5bef983
Source dataset
uspto-grants-1986_04
Patent number
US04579956

Reaction notes

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