Hydrochloric Acid → Hydrochloric Acid

HRID 1837188Notes

Reaction equation

HRID 1837188 reaction equation
[CH3:1][O:2][C:3]1([C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=2)[C:15]#[N:16])[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[CH2:9][NH:10][CH3:11].[ClH:20]>CC(OC)(C)C>[ClH:20].[CH3:1][O:2][C:3]1([C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=2)[C:15]#[N:16])[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[CH2:9][NH:10][CH3:11].[ClH:20]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10125309HCID 10125309, compound

Product 2

HCID 313Hydrochloric AcidYield 5,774%HCID 69981714HCID 69981714, 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-(1-Methoxy-2-methylaminomethyl-cyclohexyl)-benzonitrile (0.10 g, 0.038 mmol). To the flask was added 5 mL of dry MTBE. 2N HCl (0.38 mL, 0.76 mmol) was added dropwise at room temperature. After stirring for 1 hour at room temperature, the white precipitate was filtered in vacuo to provide 0.08 g (91%) of HCl salt. 1H NMR (CDCl3) 1.23-2.09 (m, 14H), 2.82 (m, 1H), 3.22 (s, 3H), 7.59 (m, 4H). 13C NMR (75 MHz, CDCl3) 21.4, 24.9, 26.1, 31.9, 34.1, 44.8, 50.5, 80.2, 112.9, 118.8, 129.8, 130.0, 131.1, 144.2. Mass spectrum (m/e) 260.2 (M+).

Workup

  1. filtrationthe white precipitate was filtered in vacuo

Sources & evidence

ORD record
ord-3bfe916f724c47febc84f6ee534d7a46
Source dataset
uspto-grants-2004_08
Patent number
US06780891B2

Reaction notes

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