HCID 86699737, compound → HCID 72187888, compound

HRID 515167Notes

Reaction equation

HRID 515167 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](=[O:27])[C:11]2[C:16]([CH3:17])=[CH:15][C:14]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:13][C:12]=2[C:24]([CH3:26])=[CH2:25])=[CH:4][CH:3]=1>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](=[O:27])[C:11]2[C:16]([CH3:17])=[CH:15][C:14]([N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)=[CH:13][C:12]=2[CH:24]([CH3:25])[CH3:26])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 86699737HCID 86699737, compound

Product 1

HCID 72187888HCID 72187888, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-[(4-chlorophenyl)-methyl]-2-isopropenyl-6-methyl-4-morpholin-4-yl-benzamide (0.19 g, 0.49 mmol) in ethyl acetate is degassed and flushed with argon for 10 min followed by the addition of Pearlman's catalyst (20% Pd(OH)2/C, 0.08 g). The resulting mixture is stirred under an atmosphere of hydrogen for 2 h. After completion of reaction (monitored by NMR), the reaction mixture is filtered through a pad of celite. The filtrate is concentrated and the residue is purified by preparative HPLC affording N-[(4-chlorophenyl)-methyl]-2-isopropyl-6-methyl-4-morpholin-4-yl-benzamide (example 14) (0.075 g, 0.28 mmol, 57%). [M+H]+ 387.2.

Workup

  1. customflushed with argon for 10 min
  2. additionfollowed by the addition of Pearlman's catalyst (20% Pd(OH)2/C, 0.08 g)
  3. customAfter completion of reaction (monitored by NMR)
  4. filtrationthe reaction mixture is filtered through a pad of celite
  5. concentrationThe filtrate is concentrated
  6. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-d6b028f027d1441ab16ff80c5be1541b
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

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