Water → HCID 68292042, compound

HRID 2404589Notes

Reaction equation

HRID 2404589 reaction equation
O.C[Si]([Cl:6])(C)C.[CH3:7][N:8]([CH2:10][CH:11]1[CH:17]([C:18]2[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=2)[CH2:16][CH:15]2[CH2:25][CH:12]1[CH2:13][CH2:14]2)[CH3:9]>CC(=O)CC>[ClH:6].[CH3:9][N:8]([CH2:10][CH:11]1[CH:17]([C:18]2[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=2)[CH2:16][CH:15]2[CH2:25][CH:12]1[CH2:13][CH2:14]2)[CH3:7]

Participants

5

Reactant 3

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 60151906HCID 60151906, compound

Product 1

HCID 68292042HCID 68292042, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Add H2O (70 mg, 3.89 mmol) and TMSCl (126 mg, 1.17 mmol) to a solution of 3-(2-dimethylaminomethyl-bicyclo[3.2.1]oct-3-yl)-phenol (252 mg, 0.97 mmol) in 2-butanone (30 ml). Then stir the reaction mixture at ambient temperature for 12 hours. Evaporate the mixture under vacuum to give 3-(2-dimethylaminomethyl-bicyclo[3.2.1]oct-3-yl)-phenol hydrochloride as white solid (286 mg, Yield: 99.8%). 1H NMR (400 MHz, D2O) δ 7.04-7.07 (t, J=10.4, 1H), 6.58-6.72 (m, 3H), 2.80-2.91 (m, 1H), 2.52-2.54 (m, 3H), 2.44-2.48 (m, 3H), 2.33-2.41 (m, 1H), 2.20-2.29 (m, 1H), 2.11 (s, 1H), 1.99 (s, 2H), 1.36-1.47 (m, 8H).

Workup

  1. customEvaporate the mixture under vacuum

Sources & evidence

ORD record
ord-4fa42e600fac4f25917017f873c86615
Source dataset
uspto-grants-2014_08
Patent number
US08802728B2

Reaction notes

Loading…