Hydrochloric Acid → HCID 68503104, compound

HRID 1176468Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:52]=[CH:51][CH:50]=[CH:49][C:4]=1[CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[CH2:19][CH:18]2[O:33][CH2:34][CH2:35][O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[CH2:43][CH2:44][C:45]([O:47]C)=[O:46])=[CH:13][CH:12]=1.[OH-].[Na+].Cl>O1CCOCC1.[Cl-].[Na+].O>[C:45]([CH2:44][CH2:43][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=1[O:36][CH2:35][CH2:34][O:33][CH:18]1[CH:17]([C:14]2[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][CH2:7][O:6][CH2:5][C:4]3[CH:49]=[CH:50][CH:51]=[CH:52][C:3]=3[O:2][CH3:1])=[CH:16][CH:15]=2)[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH2:19]1)([OH:47])=[O:46]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 0.16 g of benzyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-{2-[2-(2-methoxycarbonylethyl)phenoxy]ethoxy}piperidine-1-carboxylate in 4 ml of dioxane is admixed with 0.4 ml of 2N NaOH and stirred at 80° C. over 3 hours. The reaction mixture is cooled to room temperature and acidified to pH 6 with 1N HCl. The solution is admixed with brine and extracted with ethyl acetate (2×). The combined organic phases are dried over sodium sulphate and concentrated by evaporation. The crude title compound is obtained as a yellow foam from the residue. Rt=5.64.

Workup

temperatureThe reaction mixture is cooled to room temperature
extractionextracted with ethyl acetate (2×)
dry with materialThe combined organic phases are dried over sodium sulphate
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-a80b90c1a9824282881af0059cc668ab
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842688B2

Reaction notes

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