HCID 86699735, compound → HCID 72187886, compound

HRID 515166Notes

Reaction equation

HRID 515166 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](=[O:26])[C:11]2[C:16]([CH:17]=[CH2:18])=[CH:15][C:14]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[CH:13][C:12]=2[CH3:25])=[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:26])[C:11]2[C:12]([CH3:25])=[CH:13][C:14]([N:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)=[CH:15][C:16]=2[CH2:17][CH3:18])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 86699735HCID 86699735, compound

Product 1

HCID 72187886HCID 72187886, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-[(4-chlorophenyl)-methyl]-2-methyl-4-morpholin-4-yl-6-vinyl-benzamide (0.18 g, 0.48 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-ethyl-6-methyl-4-morpholin-4-yl-benzamide (example 12) (0.105 g, 0.28 mmol, 59%). [M+H]+ 373.2.

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-d30d499cd0344bbcba9cbdb54ce63c63
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

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