Acetonitrile → HCID 23141667, compound

HRID 32160Notes

Reaction equation

[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[C:11]([C:21]3[CH2:26][CH2:25][C:24]4([CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]4)[CH2:23][CH:22]=3)[CH:10]=2)[CH2:5][CH2:4]1.[CH3:32][O:33][CH2:34][CH2:35]Br.C(=O)([O-])[O-].[K+].[K+].C(#N)C>[Cl-].[Na+].O.C(OCC)(=O)C>[CH3:32][O:33][CH2:34][CH2:35][N:18]1[CH2:19][CH2:20][N:15]([C:12]2[CH:13]=[CH:14][C:9]([N:6]3[CH2:7][CH2:8][CH:3]([O:2][CH3:1])[CH2:4][CH2:5]3)=[CH:10][C:11]=2[C:21]2[CH2:26][CH2:25][C:24]3([CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[CH2:23][CH:22]=2)[CH2:16][CH2:17]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-[4-(4-methoxypiperidin-1-yl)-2-spiro[5.5]undec-2-en-3-yl-phenyl]piperazine (20 mg, 0.0472 mmol) produced in Example (39e), 2-bromoethyl methyl ether (0.0049 mL, 0.0519 mmol), potassium carbonate (11.1 mg, 0.0803 mmol) and acetonitrile (1 mL) was stirred for 5 hours at an external temperature of 80° C. Ethyl acetate and brine were added to the reaction mixture and extraction was performed three times with ethyl acetate. The separated organic layers were concentrated. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 1-(2-methoxyethyl)-4-[4-(4-methoxypiperidin-1-yl)-2-spiro[5.5]undec-2-en-3-ylphenyl]piperazine.

Workup

concentrationThe separated organic layers were concentrated
customThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-1e8ff9f29ad6468683b34d1fe9ea5440
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425554B2

Reaction notes

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