(+-)-3-Quinuclidinol → 3-Quinuclidinyl 1-(4-chlorophenyl)cyclobutanecarboxylate Hydrochloride

HRID 1955274Notes

Reaction equation

HRID 1955274 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12](Cl)=[O:13])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[N:15]12[CH2:22][CH2:21][CH:18]([CH2:19][CH2:20]1)[CH:17]([OH:23])[CH2:16]2>>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:12]([O:23][CH:17]3[CH:18]4[CH2:21][CH2:22][N:15]([CH2:20][CH2:19]4)[CH2:16]3)=[O:13])[CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 15381(+-)-3-QuinuclidinolHCID 130833731-(4-Chlorophenyl)cyclobutane-1-carbonyl chloride

Product 1

HCID 232950713-Quinuclidinyl 1-(4-chlorophenyl)cyclobutanecarboxylate Hydrochloride

Procedure

The title compound was prepared in an analogous manner to that in Example 36 by reacting 1-(4-chlorophenyl)-cyclobutanecarbonyl chloride with 3-quinuclidinol at 80° C. for 25 h. The yield was 0.7 g (43%); mp 205-208° C.; 1H NMR (D2O) δ 1.73-1.85 (m, 2H), 1.86-1.97 (m, 2H), 2.04-2.15 (m, 2H), 2.32 (m, 1H), 2.48-2.63 (m, 2H), 2.87 (m, 2H), 3.12 (m, 1H), 3.22 (d, 1H), 3.27-3.42 (m, 3H), 3.73 (m, 1H), 5.17 (m, 1H), 7.37 (d, 2H), 7.43 (d, 2H). Anal. (C18H22ClNO2.HCl) C, H, N.

Workup

  1. customat 80° C.
  2. customfor 25 h

Sources & evidence

ORD record
ord-7043b02b5a8941aea2a4dfbab3b9ee56
Source dataset
uspto-grants-2000_09
Patent number
US06124354

Reaction notes

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