Morpholine → 4-Methyl-1-morpholinocyclohexene

HRID 1753955Notes

Reaction equation

HRID 1753955 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-c6d278a82ea448b48e7f7279902da389
Source dataset
uspto-grants-2015_10
Patent number
US09168317B2

Reaction notes

Loading…