Hydrochloric Acid → HCID 86717924, compound

HRID 2275841Notes

Reaction equation

HRID 2275841 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].CO.C(OCC)C>[ClH:28].[ClH:28].[NH2:1][CH2:2][C:3]1([NH2:7])[CH2:6][O:5][CH2:4]1

Participants

8

Reactant 3

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

Product 1

HCID 86717924HCID 86717924, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 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. The mixture was then filtered through a Millipore® filter, the filter cake was washed with methanol, 2.6 ml (5.2 mmol) of 2 M hydrogen chloride in diethyl ether were added to the filtrate and the mixture was 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. filtrationThe mixture was then filtered through a Millipore®
  3. filtrationfilter
  4. additionwere added to the filtrate
  5. concentrationthe mixture was concentrated
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-9fb7f2ee48fd43ef91118805b4e55cc1
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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