Hydrochloric Acid → HCID 86717924, compound

HRID 1486250Notes

Reaction equation

HRID 1486250 reaction equation
[NH2:1][CH2:2][C:3]1([N:7](CC2C=CC=CC=2)CC2C=CC=CC=2)[CH2:6][O:5][CH2:4]1.C1CCCCC=1.[ClH:28]>C(O)C.[Pd].C(OCC)C>[ClH:28].[ClH:28].[NH2:1][CH2:2][C:3]1([NH2:7])[CH2:6][O:5][CH2:4]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8079CyclohexeneHCID 574158213-(aminomethyl)-N,N-dibenzyloxetan-3-amine

Product 1

HCID 86717924HCID 86717924, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

585 mg (2.07 mmol) of 3-(aminomethyl)-N,N-dibenzyloxetane-3-amine [synthesis described in: US2008/103183 A1, 2008; p. 48] were initially charged in ethanol (29.2 ml), and 441 mg (0.41 mmol) of 10% palladium on activated carbon and 6.3 ml (62.2 mmol) of cyclohexene were added. The reaction mixture was stirred under reflux for 8 h. Subsequently, the reaction mixture was filtered through a Millipore® filter and washed with methanol, and the filtrate was admixed with 2.6 ml (5.2 mmol) of 2 M hydrogen chloride in diethyl ether, concentrated and dried under high vacuum. This gave 423 mg (87% of theory, purity 75%) of the target compound.

Workup

  1. temperatureunder reflux for 8 h
  2. filtrationSubsequently, the reaction mixture was filtered through a Millipore®
  3. filtrationfilter
  4. washwashed with methanol
  5. concentrationconcentrated
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-d74e2a2158404e58b0811aabcd1e4cb0
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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