Hydrochloric Acid → Hydrochloric Acid

HRID 1837186Notes

Reaction equation

HRID 1837186 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17])[O:11][CH3:12])[CH3:3].[ClH:21]>CC(OC)(C)C>[ClH:21].[CH3:1][N:2]([CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17])[O:11][CH3:12])[CH3:3].[ClH:21]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 23497857HCID 23497857, compound

Product 2

HCID 313Hydrochloric AcidYield 5,907.3%HCID 69981052HCID 69981052, 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 (+/−)-3-(2-Dimethylaminomethyl-1-methoxy-cyclohexyl)-benzonitrile (0.25 g, 0.091 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 0.196 g (70%) of HCl salt. 1H NMR (CD3OD) 1.48-2.09 (m, 9H), 2.26 (s, 3H), 2.53 (m, 1H), 2.62 (s, 3H), 2.94 (m, 1H), 3.18 (s, 3H), 7.60 (m, 4H). 13C NMR (75 MHz, CDCl3) 21.1, 24.8, 27.7, 31.9, 41.8, 43.9, 46.0, 50.4, 59.8, 79.7, 112.8, 118.7, 129.9, 130.0, 131.1, 131.2, 144.5. Mass spectrum (m/e) 274.5 (M+).

Workup

  1. filtrationthe white precipitate was filtered in vacuo

Sources & evidence

ORD record
ord-02ac0e830df34b8a8bdd96bc0e34b541
Source dataset
uspto-grants-2004_08
Patent number
US06780891B2

Reaction notes

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