Hydrochloric Acid → 4-(Morpholin-4-yl)cyclohexan-1-one

HRID 1924473Notes

Reaction equation

HRID 1924473 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[CH2:7][CH2:6]2)[O:4]CC1.Cl>C1COCC1>[N:11]1([CH:8]2[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]2)[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 534863564-(1,4-Dioxaspiro[4.5]decan-8-yl)morpholine

Product 1

HCID 567638304-(Morpholin-4-yl)cyclohexan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7 (4.50 g, 19.8 mmol) in THF (100 mL) was added 7 N aqueous HCl (40 mL). The reaction mixture was stirred for 17 h and the reaction was quenched by pouring onto saturated aqueous NaHCO3 (475 mL). The mixture was extracted with EtOAc (1×) then CH2Cl2 (3×) and the combined organic extracts dried (MgSO4) and concentrated. The resulting oil was purified by Kugelrohr distillation to give (VII-g) (3.17 g, 87%) as a clear oil; 1H NMR (400 MHz, CDCl3) δ 1.80-1.94 (m, 2H), 1.80-2.10 (m, 2H), 2.30 (m, 1H), 2.45-2.65 (m, 8H), 3.74 (t, J=4.7 Hz, 4H).

Workup

  1. customthe reaction was quenched
  2. additionby pouring onto saturated aqueous NaHCO3 (475 mL)
  3. extractionThe mixture was extracted with EtOAc (1×)
  4. dry with materialCH2Cl2 (3×) and the combined organic extracts dried (MgSO4)
  5. concentrationconcentrated
  6. distillationThe resulting oil was purified by Kugelrohr distillation
  7. customto give (VII-g) (3.17 g, 87%) as a clear oil

Sources & evidence

ORD record
ord-26ec8332c16a4aaba056d5215b13e0d4
Source dataset
uspto-grants-2012_05
Patent number
US08178552B2

Reaction notes

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