Hydrochloric Acid → HCID 178453601, compound

HRID 322495Notes

Reaction equation

HRID 322495 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([CH2:16][NH2:17])[CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[ClH:20].O1CCOCC1>C(OCC)C>[ClH:20].[C:1]([O:5][C:6]([NH:8][CH2:9][C@H:10]1[CH2:11][CH2:12][C@H:13]([CH2:16][NH2:17])[CH2:14][CH2:15]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 312751,4-DioxaneHCID 178453600HCID 178453600, compound

Product 1

HCID 178453601HCID 178453601, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethanol (40 mL) was added to N-tert-butoxycarbonyl-trans-4-(aminomethyl)cyclohexanemethyl azide (1.79 g, 6.67 mmol.) and 5% palladium on carbon (270 mg, 0.15 wt. %) under nitrogen. The reaction mixture was stirred under hydrogen at atmospheric pressure for 6 hours at 23° C. The black suspension was filtered and the filtrate concentrated to give N-tert-butoxycarbonyl-trans-1,4-cyclohexane bis(methylamine) as a yellow oil. The crude amine was taken up into methanol (2.0 mL) followed by addition of hydrogen chloride in dioxane (4.0 M, 2.0 mL, 8.0 mmol.) and ethyl ether (25 mL). The resulting precipitate was collected by filtration to give N-tert-butoxycarbonyl-trans-1,4-cyclohexanebis(methylamine) hydrochloride (1.42 g, 76% yield) as a colorless solid.

Workup

  1. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-4cc7202d08ff4f93a056b21ecac02178
Source dataset
uspto-grants-2001_04
Patent number
US06211228B1

Reaction notes

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