Hydrochloric Acid → Hydrochloric Acid

HRID 1837184Notes

Reaction equation

HRID 1837184 reaction equation
[CH3:1][O:2][C@:3]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7][CH2:6][CH2:5][C@@H:4]1[CH2:9][N:10]([CH3:12])[CH3:11].[ClH:19]>CC(OC)(C)C>[ClH:19].[CH3:1][O:2][C@:3]1([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:8][CH2:7][CH2:6][CH2:5][C@@H:4]1[CH2:9][N:10]([CH3:12])[CH3:11].[ClH:19]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 44455135HCID 44455135, compound

Product 2

HCID 313Hydrochloric AcidYield 685.7%HCID 69917245HCID 69917245, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

The HCl salt was prepared as follows. To a 50 mL RBF under argon was charged with (1R,2R)-(2-methoxy-2-phenyl-cyclohexylmethyl)-dimethyl-amine (0.27 g, 1.09 mmol). To the flask was added 5 mL of dry MTBE. 2N HCl (0.80 mL, 1.60 mmol) was added dropwise at room temperature. After stirring for 1 hour at room temperature, the white precipitate was filtered in vacuo to provide 0.20 g (64%) of HCl salt. 1H NMR (CDCl3) 1.45-1.97 (m, 7H), 2.10 (s, 3H), 2.14 (m, 1H), 2.38 (d, J=11.3 Hz, 1H), 2.54 (s, 3H), 2.73 (d, J=12.4 Hz, 1H), 2.86 (dd, J=7.7, 12.8 Hz, 1H), 3.22 (s, 3H), 7.28 (m, 3H), 7.39 (m, 2H). 13C NMR (75 MHz, CDCl3) 22.8, 25.6, 28.2, 32.5, 42.4, 44.8, 45.7, 50.7, 61.3, 81.4, 127.9, 128.6, 129.9, 143.5. Mass spectrum (m/e) 249.0 (M+).

Workup

  1. filtrationthe white precipitate was filtered in vacuo

Sources & evidence

ORD record
ord-e040ee7a6102426fbbae2c612e78dc08
Source dataset
uspto-grants-2004_08
Patent number
US06780891B2

Reaction notes

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