Hydrochloric Acid → HCID 21472435, compound

HRID 2294952Notes

Reaction equation

HRID 2294952 reaction equation
C(C1C=CC=CC=1O)C=C.C(OC1C=CC(O)=CC=1)CCC.[CH2:23]([C:26]1[CH:42]=[CH:41][CH:40]=[CH:39][C:27]=1[O:28][CH2:29][C:30]1([OH:38])[CH:35]2[CH2:36][CH2:37][N:32]([CH2:33][CH2:34]2)[CH2:31]1)[CH:24]=[CH2:25].[ClH:43]>CC(C)=O.CCOCC>[ClH:43].[CH2:23]([C:26]1[CH:42]=[CH:41][CH:40]=[CH:39][C:27]=1[O:28][CH2:29][C:30]1([OH:38])[CH:35]2[CH2:36][CH2:37][N:32]([CH2:33][CH2:34]2)[CH2:31]1)[CH:24]=[CH2:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 156242-AllylphenolHCID 312334-ButoxyphenolHCID 21472424HCID 21472424, compound

Product 1

HCID 21472435HCID 21472435, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

The procedure described in Example 1 was repeated using 2-allylphenol (9.6 g), instead of 4-butoxyphenol, to prepare 3-(2-allylphenoxymethyl)-3-hydroxyquinuclidine which was dissolved in acetone and a solution of hydrogen chloride in ether added to afford 3-(2-allylphenoxymethyl)-3-hydroxyquinuclidine hydrochloride as a colourless solid, m.p. 102°-128° C.; microanalysis, found: C, 64.7; H, 8.0; N, 4.5% C17H23NO2.HCl.0.3H2O requires C, 64.8; H, 7.9; N, 4.4%; NMR (DMSO-d6): 1.6-1.8(1H, m), 1.7-2.0(2H, m), 2.1-2.3(2H, m), 3.0-3.5(8H, m), 4.0-4.1(2H, q), 5.0-5.1(2H, m), 5.5(1H, s), 5.9-6.1(1H, m), 6.8-7.0(2H, m), 7.1-7.3(2H, m) and 10.7(1H, br); m/z 274 (M+H).

Sources & evidence

ORD record
ord-fff1a4f7e8fa4f3ea264924837ac1213
Source dataset
uspto-grants-1997_11
Patent number
US05691349

Reaction notes

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