Hydrogen Bromide → Hydrogen Bromide

HRID 2225306Notes

Reaction equation

HRID 2225306 reaction equation
[C:1]([CH2:3][C@@H:4]1[CH2:9][C@H:8]([N:10]([CH:12]([CH3:14])[CH3:13])[CH3:11])[CH2:7][CH2:6][C@@H:5]1[NH:15]C(=O)[O-])#[N:2].[BrH:19]>C(O)(=O)C>[NH2:15][C@H:5]1[CH2:6][CH2:7][C@@H:8]([N:10]([CH:12]([CH3:14])[CH3:13])[CH3:11])[CH2:9][C@H:4]1[CH2:3][C:1]#[N:2].[BrH:19]

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 86596974HCID 86596974, compound

Product 2

HCID 260Hydrogen BromideHCID 69285582HCID 69285582, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of (1S,2S,4R)-2-(cyanomethyl)-4-(isopropyl(methyl)amino)cyclohexylcarbamate (479 mg) in 4 ml of acetic acid was added 4 ml of 30% HBr in acetic acid, and the mixture was stirred for 2.5 hours. The acid was evaporated off under reduced pressure and residue was dried by azeotroping with benzene several times. The residue was further dried under vacuum to give 2-((1S,2S,5R)-2-amino-5-(isopropyl(methyl)amino)cyclohexyl)acetonitrile as a bis-HBr salt as a solid (673 mg).

Workup

  1. customThe acid was evaporated off under reduced pressure and residue
  2. customwas dried
  3. customby azeotroping with benzene several times
  4. customThe residue was further dried under vacuum

Sources & evidence

ORD record
ord-9badaf30b97f453ba76d28eddcc15f50
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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