Butyl ether → HCID 45262091, compound

HRID 566530Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][N:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[NH:22]1[CH2:27][CH2:26][CH2:25][C@@H:24]([C:28]([O:30]CC)=[O:29])[CH2:23]1.C(=O)([O-])[O-].[K+].[K+].C(OCCCC)CCC>>[ClH:1].[C:10]1([N:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4][CH2:3][CH2:2][N:22]2[CH2:27][CH2:26][CH2:25][C@@H:24]([C:28]([OH:30])=[O:29])[CH2:23]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Reactant 4

HCID 8909Butyl ether

HCID 11430Potassium Carbonate

HCID 185582ethyl (3R)-piperidine-3-carboxylate

HCID 10733265HCID 10733265, compound

Product 1

HCID 45262091HCID 45262091, compound

Conditions

Temperature: 150 °C

Procedure

A mixture of 1-chloro-4-(2-(diphenylamino)ethoxy)butane (2.0 g, 6.6 mmol), ethyl (R)-3-piperidinecarboxylate (1.1 g, 7.0 mmol), potassium carbonate (1.0 g, 7.2 mmol) and dry dibutylether was heated at 150° C. for 4 h. The mixture was cooled, filtered and the solvent evaporated in vacuo. The residue was submitted to flash chromatography on silica gel (150 g) using a mixture of n-heptane and THF (4:1) as eluent. This afforded 1.5 g (34% calculated from 2-(diphenylamino)ethanol) of

Workup

temperatureThe mixture was cooled
filtrationfiltered
customthe solvent evaporated in vacuo
additiona mixture of n-heptane and THF (4:1) as eluent

Sources & evidence

ORD record: ord-fdbe445d9b9f4145858645b07fb01dc0
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06174898B1

Reaction notes

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