Hydrochloric Acid → HCID 178511675, compound

HRID 2268418Notes

Reaction equation

HRID 2268418 reaction equation
[CH2:1]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([NH:15]C(=O)OC(C)(C)C)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>ClCCl>[NH2:15][C@H:12]1[CH2:13][CH2:14][C@H:9]([NH:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178454034HCID 178454034, compound

Product 1

HCID 178511675HCID 178511675, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of tert-butyl trans-4-(benzylamino)cyclohexylcarbamate (730 mg, 3.6 mmol) (preparation 26) in dichloromethane (20 ml) was saturated with hydrogen chloride gas. The reaction mixture was stirred at room temperature for 2 hr and the solvent removed under reduced pressure to give a residue which was triturated with diethyl ether. The resulting solid was dissolved in water and solid sodium hydrogen carbonate added. The aqueous mixture was then extracted with ethyl acetate followed by dichloromethane. The organic extracts were combined, the solvent removed under reduced pressure and the residue purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (95:5:0.5) to give the title compound (530 mg) as a gum.

Workup

  1. customthe solvent removed under reduced pressure
  2. customto give a residue which
  3. customwas triturated with diethyl ether
  4. dissolutionThe resulting solid was dissolved in water
  5. additionsolid sodium hydrogen carbonate added
  6. extractionThe aqueous mixture was then extracted with ethyl acetate
  7. customthe solvent removed under reduced pressure
  8. customthe residue purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (95:5:0.5)

Sources & evidence

ORD record
ord-cec4b4c540d940e9b99b33bb914ce98b
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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