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

HRID 2408524Notes

Reaction equation

Cl.O1[C:6]2([CH2:11][CH2:10][CH:9]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[CH2:8][CH2:7]2)[O:5]CC1.Cl.C([O-])(O)=O.[Na+]>C1COCC1>[N:12]1([CH:9]2[CH2:8][CH2:7][C:6](=[O:5])[CH2:11][CH2:10]2)[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 4-(1,4-dioxa-spiro[4.5]dec-8-yl)-morpholine hydrochloride (6.79 g, 25.7 mmol, as prepared in the previous step) in THF (100 mL) was treated with HCl (38.6 mL, 77.2 mmol, 2M aq) and heated to 80° C. for 4 h. The cooled mixture was treated with satd aq NaHCO3 to pH 7 and extracted with ether (3×250 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo to afford the title compound (2.22 g, 47%) as a colorless oil. 1H-NMR (CDCl3; 400 MHz): δ 3.78-3.72 (m, 4H), 2.60-2.55 (m, 4H), 2.36-2.25 (m, 2H), 2.09-1.99 (m, 2H), 1.93-1.82 (m, 2H).

Workup

extractionextracted with ether (3×250 mL)
dry with materialThe combined organic layers were dried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f09cbd841e694c1fb34c9968a8ab001c
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815867B2

Reaction notes

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