Morpholine → 4-Methyl-1-morpholinocyclohexene

HRID 1506714Notes

Reaction equation

HRID 1506714 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-e2220a7fc20742579432e9eab6129f5e
Source dataset
uspto-grants-2015_12
Patent number
US09220795B2

Reaction notes

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