Benzylamine → 40571-86-6

HRID 2363896Notes

Reaction equation

HRID 2363896 reaction equation
[CH:1]12[O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6]2.[CH2:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O>[CH2:8]([NH:15][C@@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C@H:1]1[OH:7])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 9246Cyclohexene oxide

Product 1

HCID 272465040571-86-6

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of cyclohexene oxide (1) (19 mL, 0.2 mol, Aldrich cat #C10, 280-4) and benzylamine (27) (21 mL, 0.2 mol, Aldrich cat #407712) in water (5 mL) was refluxed for 3 hours. The cooled reaction mixture was partitioned between 4M aq NaOH (100 mL) and methyl t-butyl ether (150 mL). The aqueous layer was further extracted with methyl t-butyl ether (2×100 mL), and the combined organic extracts were dried over anhydrous magnesium sulfate and concentrated in vacuo to give trans-2-benzylaminocyclohexan-1-ol (28) as a low melting point solid (39.4 g, 96% yield);

Workup

  1. temperaturewas refluxed for 3 hours
  2. customThe cooled reaction mixture
  3. customwas partitioned between 4M aq NaOH (100 mL) and methyl t-butyl ether (150 mL)
  4. extractionThe aqueous layer was further extracted with methyl t-butyl ether (2×100 mL)
  5. dry with materialthe combined organic extracts were dried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d3396279903d43faade8ca0baaa7851f
Source dataset
uspto-grants-2014_04
Patent number
US08692002B2

Reaction notes

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