Triethylamine → 3-bromo-N-cyclopropyl-5-(3-methoxypropyl)-4-methylbenzamide

HRID 337631Notes

Reaction equation

HRID 337631 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([C:15]#[C:16][CH2:17][O:18][CH3:19])[C:13]=1[CH3:14])[C:5]([NH:7][CH:8]1[CH2:10][CH2:9]1)=[O:6].C(N(CC)CC)C>C1(C)C=CC=CC=1.[Pt]=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([CH2:15][CH2:16][CH2:17][O:18][CH3:19])[C:13]=1[CH3:14])[C:5]([NH:7][CH:8]1[CH2:10][CH2:9]1)=[O:6]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 581710363-Bromo-N-cyclopropyl-5-(3-methoxy-prop-1-ynyl)-4-methyl-benzamide

Product 1

HCID 581710133-bromo-N-cyclopropyl-5-(3-methoxypropyl)-4-methylbenzamide

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 1140TolueneSolvent

Procedure

To a stirred solution of 3-bromo-N-cyclopropyl-5-(3-methoxy-prop-1-ynyl)-4-methyl-benzamide and platinum oxide (0.04 equiv.) in toluene (˜0.12 M) was added triethylamine (0.2 equiv.). The resultant solution was hydrogenated at 1.8 Barg for 3 h and then filtered to remove the catalyst. The solution was concentrated to ˜4 volumes and then heptane added (8 volumes). The resultant slurry was filtered to afford the product as an off-white solid. 1H NMR (500 MHz, Acetone-d6): δ 7.87 (m, 2 H), 7.65 (s, 1 H), 3.35 (t, J=6.12 Hz, 2 H), 3.27 (s, 3 H), 2.93-2.86 (m, 1 H), 2.75 (t, J=7.91 Hz, 2 H); 2.39 (s, 3 H), 1.80-1.72 (m, 2 H), 0.75-0.67 (m, 2 H), 0.61-0.56 (m, 2 H). HRMS (ES, M+H) Calcd 326.0767. Found 326.0756.

Workup

  1. filtrationfiltered
  2. customto remove the catalyst
  3. concentrationThe solution was concentrated to ˜4 volumes
  4. additionheptane added (8 volumes)
  5. filtrationThe resultant slurry was filtered

Sources & evidence

ORD record
ord-47ccd707ba174c7ba2859d52e71df5e7
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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