Hydrochloric Acid → 4-Aminocyclohexanone Hydrochloride

HRID 490901Notes

Reaction equation

HRID 490901 reaction equation
[ClH:1].[O:2]=[C:3]1[CH2:8][CH2:7][CH:6]([NH:9]C(=O)OC(C)(C)C)[CH2:5][CH2:4]1>O1CCOCC1>[ClH:1].[NH2:9][CH:6]1[CH2:7][CH2:8][C:3](=[O:2])[CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamate

Product 1

HCID 426145974-Aminocyclohexanone Hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of hydrogen chloride in dioxan (0.5 ml, 2.0 mmol, 4M) was added to a stirred solution of tert-butyl 4-oxocyclohexylcarbamate (0.043 g, 0.20 mmol, commercially available from Astatech Inc., Philadelphia, USA) in dioxan (0.5 ml) and the mixture was stirred at room temperature. After 1 h, the reaction mixture was evaporated to give Intermediate 56 as a cream solid (34 mg). 1H NMR (400 MHz in d6-DMSO, 27° C., δ ppm) 8.09 (br. s, 3H), 3.51 (tt, 11, 3.5 Hz, 1H), 2.45 (m, 2H, partially obscured), 2.29 (m, 2H), 2.16 (m, 2H), 1.76 (m, 2H).

Workup

  1. customthe reaction mixture was evaporated

Sources & evidence

ORD record
ord-340870252fde457287c88bb0fe3c68e9
Source dataset
uspto-grants-2009_05
Patent number
US07528148B2

Reaction notes

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