Methanol → HCID 90060571, compound

HRID 1055389Notes

Reaction equation

HRID 1055389 reaction equation
C([N:8](CC1C=CC=CC=1)[CH:9]1[C:15]2([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[O:14][C:13]2[CH:21]=[CH:22][CH:23]=[CH:24][C:12]=2[NH:11][C:10]1=[O:25])C1C=CC=CC=1.CO>[OH-].[OH-].[Pd+2].C(O)(=O)C>[NH2:8][CH:9]1[C:15]2([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)[O:14][C:13]2[CH:21]=[CH:22][CH:23]=[CH:24][C:12]=2[NH:11][C:10]1=[O:25]

Participants

5

Reactant 2

HCID 887MethanolHCID 90037478HCID 90037478, compound

Product 1

HCID 90060571HCID 90060571, compoundYield 132.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

3-(Dibenzylamino)-3H-spiro[benzo[b][1,4]oxazepine-2,1′-cyclohexan]-4 (5H)-one (0.3875 g, 908 μmol, Eq: 1.00) and 20% Pd(OH)2/C (0.47 g, 3.35 mmol, Eq: 3.68) were combined with MeOH (100 mL) and acetic acid (0.1 mL) and the mixture was hydrogenated at 50 psi. After 18 h, the mixture was filtered through Celite, the filtrate concentrated, the residue dissolved in MeCN/H2O and lyophilized to afford of the title compound as an off-white solid (0.297 g, 100%) which was used without purification. MS m/z 247.0 (MH+)

Workup

  1. filtrationthe mixture was filtered through Celite
  2. concentrationthe filtrate concentrated
  3. dissolutionthe residue dissolved in MeCN/H2O

Sources & evidence

ORD record
ord-17af006abde3463a8ecc007d4e4f49b0
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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