Hydrochloric Acid → Delmopinol hydrochloride

HRID 1099534Notes

Reaction equation

[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH:5]1[CH2:10][CH2:11][CH2:12][CH:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16].[ClH:20]>C(C(C)=O)C(C)C>[ClH:20].[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH:5]1[CH2:10][CH2:11][CH2:12][CH:13]([CH2:14][CH2:15][CH3:16])[CH2:17][CH2:18][CH3:19]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 7.4 g of crude 4-(2-hydroxyethyl)-3-(4-propylheptyl)morpholine in 22 ml of methyl iso-butyl ketone at room temperature concentrated hydrochloric acid (2.7 g, 1 eq.) was added. The solution was concentrated until dry at 60° C. The oil was dissolved again in 21 ml of methyl iso-butyl ketone the solution was seeded and stirred for 2 hours at 0° C. The white solid was filtered, washed with 20 ml of cold methyl iso-butyl ketone and dried to obtain 5.9 g of 4-(2-hydroxyethyl)-3-(4-propylheptyl) morpholine hydrochloride (delmopinol hydrochloride). 1H-NMR (CDCl3, 400 MHz), (d ppm): 0.88 (6H, m, H15), 1.2-1.4 (13H, m), 1.8-2.0 (2H, m), 2.8-3.4 (5H, m), 3.4-4.4 (6H, m). 13C-NMR (CDCl3, 400 MHz), (d ppm): 14.26 (C15), 19.47, 19.52 (C14), 22.87 (C10), 27.11 (C9), 33.25 (C11), 35.54, 35.62 (C13), 36.59 (C12), 49.25 (C5), 53.20 (C7), 55.93 (C3), 57.08, 59.89 (C8), 63.1, 63.2, 65.0 (C6), 67.7 (C2).

Workup

concentrationThe solution was concentrated
customuntil dry at 60° C
dissolutionThe oil was dissolved again in 21 ml of methyl iso-butyl ketone the solution
filtrationThe white solid was filtered
washwashed with 20 ml of cold methyl iso-butyl ketone
customdried

Sources & evidence

ORD record: ord-56dc190d991e4057a94e4aaecc2a0e39
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143463B2

Reaction notes

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