(+-)-3-Quinuclidinol → HCID 23294956, compound

HRID 1955271Notes

Reaction equation

HRID 1955271 reaction equation
[C:1]1([C:7]2([C:11]([Cl:13])=[O:12])[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:14]12[CH2:21][CH2:20][CH:17]([CH2:18][CH2:19]1)[CH:16]([OH:22])[CH2:15]2>>[ClH:13].[C:1]1([C:7]2([C:11]([O:22][CH:16]3[CH:17]4[CH2:20][CH2:21][N:14]([CH2:19][CH2:18]4)[CH2:15]3)=[O:12])[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 15381(+-)-3-QuinuclidinolHCID 232948921-Phenylcyclobutanecarbonyl chloride

Product 1

HCID 23294956HCID 23294956, compound

Procedure

The title compound was prepared in an analogous manner to that in Example 36 by reacting 1-phenylcyclobutancarbonyl chloride with 3-quinuclidinol at 80° C. for 15 h. The yield was 0.4 g (22%); mp 163-168° C.; 1H NMR (D2O) δ 1.80 (m, 2H), 1.88-2.02 (m, 2H), 2.04-2.17 (m, 2H), 2.38 (m, 1H), 2.59-2.70 (m, 2H), 2.90 (m, 2H), 3.08 (q, 1H), 3.18 (d, 1H), 3.28-3.39 (m, 3H), 3.69 (m, 1H), 5.18 (m, 1H), 7.42 (m, 1H), 7.47-7.54 (m, 4H). Anal. (C18H23NO2.HCl.0.5H2O) C, H, N.

Workup

  1. customat 80° C.
  2. customfor 15 h

Sources & evidence

ORD record
ord-9d4f1b6edc4143d8a220e6463904f67d
Source dataset
uspto-grants-2000_09
Patent number
US06124354

Reaction notes

Loading…