Morpholine → 4-Methyl-1-morpholinocyclohexene

HRID 628735Notes

Reaction equation

HRID 628735 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1>C1C=CC=CC=1>[CH3:1][CH:2]1[CH2:7][CH2:6][C:5]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:4][CH2:3]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 115254-Methylcyclohexanone

Product 1

HCID 3060904-Methyl-1-morpholinocyclohexeneYield 70.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In a flask equipped with a dean stark, a solution of 4-methylcyclohexanone (20.1 g, 179.3 mmol, 22 mL) and morpholine (31.3 g, 359.0 mmol, 31.4 mL) were refluxed in benzene (55 mL) for 26 hours. The benzene was removed under vacuum and the crude product was purified by distillation under reduced pressure to afford 23 g (70%) of 4-(4-methyl-cyclohex-1-enyl)-morpholine (44) as an oil (b.p. 120° C. at 10 mmHg). The structure was confirmed by 1H NMR (300 MHz, CDCl3): δH 0.94 (3H, d, J=6.0 Hz, CH3), 1.15-1.35 (1H, m, CH2CH═CN), 1.50-1.80 (3H, m, CH2CH2CHCH3), 2.00-2.25 (4H, m, CH2CH═CN and CH2CH2CHCH3), 2.65-2.95 (4H, m, OCH2NCH2), 3.73 (4H, t, J=6.0 Hz, OCH2NCH2), and 4.60-4.65 (1H, m, CH2CH═CN).

Workup

  1. customThe benzene was removed under vacuum
  2. distillationthe crude product was purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-c24f359b4b4644f48840a84f963c84b5
Source dataset
uspto-grants-2016_04
Patent number
US09314541B2

Reaction notes

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