Hydrochloric Acid → 2,3,4,5-Tetrahydro-1H-benzo(d)azepine
Reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH2:15]OS(C)(=O)=O)(=O)=O.C(#[N:23])C.[OH-].[NH4+].Cl>O>[CH2:7]1[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][CH2:15][NH:23][CH2:6]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A 350 mL pressure vessel was charged with the methanesulfonic acid 2-[2-(2-methanesulfonyloxy-ethyl)-phenyl]-ethyl ester (3.2 g/10 mmol) in a 1:1 mixture of acetonitrile and ammonium hydroxide (100 mL total volume). The vessel was sealed and heated to 100° C. for one hour (pressure rises to ca. 40 psi) and then gradually allowed to cool. The reaction contents were poured into water and acidified to ca. pH 4 with concentrated hydrochloric acid. The aqueous solution was extracted with diethyl ether (100 mL), basified to pH 14 with 30% aqueous sodium hydroxide and finally extracted repeatedly with 10% methanol/methylene chloride (4×50 mL). The combined organic extracts are dried over magnesium sulfate, filtered and concentrated to afford 2,3,4,5-tetrahydro-1H-benzo[d]azepine as a pale yellow oil (1.2 g/81%) that solidifies on standing. 1H NMR (400 MHz, CDCl3) δ 7.1 (m, 4H), 2.91 (m, 8H).
Workup
- customThe vessel was sealed
- temperatureto cool
- customThe reaction contents
- extractionThe aqueous solution was extracted with diethyl ether (100 mL)
- extractionfinally extracted repeatedly with 10% methanol/methylene chloride (4×50 mL)
- dry with materialThe combined organic extracts are dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d4e1b600078944649ce4f5aa75b36cd2
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08148391B2
Reaction notes
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