Diethyl Ether → HCID 69285537, compound

HRID 2225247Notes

Reaction equation

HRID 2225247 reaction equation
[CH:1]([N:4]([CH3:25])[C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11]C(=O)OCC2C=CC=CC=2)[C@H:7]([CH2:22][O:23][CH3:24])[CH2:6]1)([CH3:3])[CH3:2].C(OCC)C>Br.C(O)(=O)C>[CH:1]([N:4]([CH3:25])[C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH2:11])[C@H:7]([CH2:22][O:23][CH3:24])[CH2:6]1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 86596948HCID 86596948, compound

Product 1

HCID 69285537HCID 69285537, compoundYield 337.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

Benzyl(1S,2R,4R)-4-(isopropyl(methyl)amino)-2-(methoxymethyl)cyclohexylcarbamate (135 mg) was dissolved in 30% HBr in acetic acid (3 ml) and stirred at rt for 45 min. Diethyl ether was added and the resulting gum was isolated, washed with additional ether, stripped four times from benzene and dried under vacuum to provide the dihydrobromide salt of (1R,3R,4S)-N1-isopropyl-3-(methoxymethyl)-N1-methylcyclohexane-1,4-diamine (280 mg) as a gum, used without further purification. MS found: (M+H)+=215.2.

Workup

  1. customthe resulting gum was isolated
  2. washwashed with additional ether
  3. customdried under vacuum

Sources & evidence

ORD record
ord-37e0d28528d94bb2b78ca597ee7ee045
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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