N-Methylbenzylamine → N-(4-{[benzyl(methyl)amino]methyl}phenyl)-1,3-dihydro-2H-isoindole-2-carboxamide

HRID 624216Notes

Reaction equation

HRID 624216 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1.C(N(C(C)C)C(C)C)C.CN1CCCC1.Cl[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]=[O:35])=[CH:29][CH:28]=1.[CH3:36][NH:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(#N)C.O>[CH2:38]([N:37]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:34]([N:2]2[CH2:3][C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:1]2)=[O:35])=[CH:29][CH:28]=1)[CH3:36])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

8

Reactant 5

HCID 7669N-MethylbenzylamineHCID 84541-MethylpyrrolidineHCID 81531DiisopropylethylamineHCID 422478IsoindolineHCID 27333194-(Chloromethyl)phenyl isocyanate

Product 1

HCID 57510227N-(4-{[benzyl(methyl)amino]methyl}phenyl)-1,3-dihydro-2H-isoindole-2-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of isoindoline (0.1 g, 0.839 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.219 ml, 1.259 mmol) in acetonitrile (2.80 ml) was treated with N-methylpyrrolidine (2.80 ml). The solution was cooled to 0° C. and 1-(chloromethyl)-4-isocyanatobenzene (0.155 g, 0.923 mmol) was added. After stirring for 2 hours at 0° C., the reaction was treated with a solution of N-methyl-1-phenylmethanamine (0.102 g, 0.839 mmol) in 0.5 mL acetonitrile. The reaction was stirred at 0° C. for 5 minutes and at ambient temperature for 30 minutes. The reaction was treated with water and the mixture was stirred for 4 hours. The suspension was filtered and the solid collected was washed with water and dried under vacuum to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.31 (s, 1H), 7.56-7.49 (m, 2H), 7.40-7.28 (m, 8H), 7.27-7.19 (m, 3H), 4.76 (bs, 4H), 3.47 (s, 2H), 3.43 (s, 2H), 2.06 (s, 3H); MS (ESI(+)) m/e 372 (M+H)+.

Workup

  1. stirringThe reaction was stirred at 0° C. for 5 minutes and at ambient temperature for 30 minutes
  2. stirringthe mixture was stirred for 4 hours
  3. filtrationThe suspension was filtered
  4. customthe solid collected
  5. washwas washed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-e6061dde516c4a0f8f3a882e62e74067
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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