Water → HCID 68292278, compound

HRID 2404585Notes

Reaction equation

HRID 2404585 reaction equation
O.C[Si]([Cl:6])(C)C.[CH3:7][N:8]([CH2:10][CH:11]1[CH:17]2[CH2:18][CH:14]([CH2:15][CH2:16]2)[CH:13]=[C:12]1[C:19]1[CH:20]=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=1)[CH3:9]>CC(=O)CC>[ClH:6].[CH3:9][N:8]([CH2:10][CH:11]1[CH:17]2[CH2:18][CH:14]([CH2:15][CH2:16]2)[CH:13]=[C:12]1[C:19]1[CH:20]=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=1)[CH3:7]

Participants

5

Reactant 3

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 60151763HCID 60151763, compound

Product 1

HCID 68292278HCID 68292278, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Add H2O (392 mg, 21.8 mmol) and TMSCl (1.4 g, 12.9 mmol) to a solution of 3-(4-dimethylaminomethyl-bicyclo[3.2.1]oct-2-en-3-yl)-phenol (2.8 g, 10.9 mmol) in 2-butanone (200 mL). Stir the reaction mixture at ambient temperature for 12 hours. Collect the precipitate by filter, and wash with EtOAc (30 mL×2), dry under vacuum to give 3-(4-dimethylaminomethyl-bicyclo[3.2.1]oct-2-en-3-yl)-phenol hydrochloride as white solid (2.41 g, Yield: 75.5%). 1H NMR (400 MHz, D2O) δ 7.20-7.24 (t, J=15.6, 1H), 6.76-6.81 (m, 2H), 6.72 (s, 1H), 6.15 (d, J=6.4, 1H), 3.58-3.61 (d, J=12.8, 1H), 3.08-3.14 (t, J=26.0, 1H), 2.89-2.92 (m, 1H), 2.88 (s, 3H), 2.76 (s, 3H), 2.56 (m, 1H), 2.45 (m, 1H), 1.72-1.83 (m, 6H).

Workup

  1. customCollect the precipitate
  2. filtrationby filter
  3. washwash with EtOAc (30 mL×2)
  4. customdry under vacuum

Sources & evidence

ORD record
ord-4030edaf4b2041deb12ed83fe59b2d45
Source dataset
uspto-grants-2014_08
Patent number
US08802728B2

Reaction notes

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