Ether hydrochloride → HCID 117857668, compound

HRID 1483159Notes

Reaction equation

HRID 1483159 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:12][CH2:11][C@:10]2([CH3:15])[C@@H:13]([CH3:14])[C@H:6]1[CH2:7][C:8]1[CH:19]=[CH:18][C:17]([C:20]([NH2:22])=[O:21])=[CH:16][C:9]=12.[ClH:23].CCOCC>C(OCC)(=O)C>[ClH:23].[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:12][CH2:11][C@:10]2([CH3:15])[C@@H:13]([CH3:14])[C@H:6]1[CH2:7][C:8]1[CH:19]=[CH:18][C:17]([C:20]([NH2:22])=[O:21])=[CH:16][C:9]=12

Participants

4

Reactant 2

HCID 10953452Ether hydrochlorideHCID 86582906HCID 86582906, compound

Product 1

HCID 117857668HCID 117857668, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R,6R,11R)-3-(2-methoxyethyl)-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methanobenzo[d]azocine-8-carboxamide (130 mg, 0.43 mmol) in ethyl acetate (10 mL) was added 2N HCl/ether (320 μL, 0.64 mmol) and the mixture stirred for 1.5 hours. The solvent was removed under reduced pressure then freeze dried giving (2R,6R,11R)-3-(2-methoxyethyl)-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methanobenzo[d]azocine-8-carboxamide hydrochloride (131 mg, 90% yield); LC/MS (M+H)+=303.22. 1H-NMR (300 MHz, DMSO) δ 10.59-10.44 (br d, 1H), 7.96 (s, 1H), 7.78 (s, 1H), 7.68 (d, 1H), 7.31 (d, 1H), 7.20 (d, 1H), 3.84-3.49 (m, 3H), 3.49-2.95 (6H+H2O), 2.43-2.20 (m, 2H), 2.16-1.97 (m, 2H), 1.54-1.23 (m, 2H), 0.87-0.66 (m, 3H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthen freeze dried

Sources & evidence

ORD record
ord-6dfee4ed254d43d4bbd39adf26dacd4e
Source dataset
uspto-grants-2016_08
Patent number
US09416137B2

Reaction notes

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