Hydrochloric Acid → 6-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-azepine hydrochloride

HRID 1507176Notes

Reaction equation

HRID 1507176 reaction equation
O[C:2]1([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH2:8][CH2:7][CH2:6][CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.[ClH:24]>>[ClH:24].[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([C:2]2[CH2:8][CH2:7][CH2:6][CH2:5][NH:4][CH:3]=2)=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 118207551HCID 118207551, compound

Product 1

HCID 1182075626-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-azepine hydrochlorideYield 96.3%

Procedure

A solution of tert-butyl 3-hydroxy-3-(4-methoxyphenyl)azepane-1-carboxylate (0.25 g, 0.78 mmol) in HCl (4M solution in dioxane) (3 mL, 12 mmol) was stirred at room temperature for 5 h. The reaction mixture was concentrated and the residue was titurated with diethyl ether to yield 6-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-azepine hydrochloride (0.18 g, 62%) as a black gum. LCMS: R.T. 0.60 min. LCMS (ES-API), m/z 204 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-ac94f1bcbbeb45feb281e496f4848db4
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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