HCID 86703348, compound → HCID 86703349, compound

HRID 2173677Notes

Reaction equation

HRID 2173677 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]([CH3:12])=[CH:10][CH2:9][CH2:8][N:7]([CH2:13][CH3:14])[C:6]=2[CH:15]=1>CO.[Pd]>[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]([CH3:12])[CH2:10][CH2:9][CH2:8][N:7]([CH2:13][CH3:14])[C:6]=2[CH:15]=1

Participants

4

Reactant 1

HCID 86703348HCID 86703348, compound

Product 1

HCID 86703349HCID 86703349, compoundYield 63.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 8-hydroxy-5-methyl-2,3-dihydro-1-ethylbenzo[b]azepine (0.14 g) and Pd/C (10 mg) in MeOH (10 mL) was purged with H2 and then stirred under 1 atm H2 for 3 hours. The reaction was then filtered over Celite, the eluent concentrated, and the crude reaction purified over silica gel (gradient of EtOAc in heptane) to provide the title compound (0.09 g) as a clear oil: 1H NMR (CDCl3) δ 7.26 (s, 1H), 6.97 (d, 1H), 6.46-6.33 (m, 2H), 3.23-3.02 (m, 4H), 2.79-2.67 (m, 2H), 1.81-1.53 (m, 3H), 1.29 (d, 3H), 1.19 (t, 3H); MS expected 206 (C13H20NO, M+1), found 206.

Workup

  1. customwas purged with H2
  2. filtrationThe reaction was then filtered over Celite
  3. concentrationthe eluent concentrated
  4. customthe crude reaction
  5. custompurified over silica gel (gradient of EtOAc in heptane)

Sources & evidence

ORD record
ord-736cf6c7e6ac4b35ba926986d47f43d4
Source dataset
uspto-grants-2015_06
Patent number
US09056885B2

Reaction notes

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