3-Phenylpropylamine → N-{4-[(3-phenylpropyl)carbamoyl]phenyl}-1,3-dihydro-2H-isoindole-2-carboxamide

HRID 624109Notes

Reaction equation

HRID 624109 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][N:2]1[C:10]([NH:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=1)=[O:11].O.ON1C2C=CC=CC=2N=N1.[C:33]1([CH2:39][CH2:40][CH2:41][NH2:42])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.O>[C:33]1([CH2:39][CH2:40][CH2:41][NH:42][C:17]([C:16]2[CH:20]=[CH:21][C:13]([NH:12][C:10]([N:2]3[CH2:1][C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH2:3]3)=[O:11])=[CH:14][CH:15]=2)=[O:19])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 162593-PhenylpropylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 62230337HCID 62230337, compound

Product 1

HCID 57509628N-{4-[(3-phenylpropyl)carbamoyl]phenyl}-1,3-dihydro-2H-isoindole-2-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-(Isoindoline-2-carboxamido)benzoic acid (150 mg, 0.531 mmol) and 1-hydroxybenzotriazole hydrate (122 mg, 0.797 mmol) were dissolved in dimethylformamide (3 ml) followed by addition of 3-phenylpropan-1-amine (110 mg, 0.797 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (153 mg, 0.797 mmol). The homogeneous solution was stirred at ambient temperature overnight. The solution was diluted with water to give a precipitate which was filtered, washed with cold ethyl acetate then ether and dried under vacuum to provide the title compound. 1H NMR (400 MHz, DMSO-d6, Temp=90° C.) δ ppm 8.27-8.34 (bs, 1H), 7.93-7.98 (m, 1H), 7.73-7.76 (m, 2H), 7.61-7.64 (m, 2H), 7.32-7.36 (m, 2H), 7.27-7.32 (m, 2H), 7.24-7.28 (m, 2H), 7.19-7.24 (m, 2H), 7.13-7.18 (m, 1H), 4.79 (s, 4H), 3.30 (q, J=6.5 Hz, 2H), 2.65 (t, J=7.6 Hz, 2H), 1.86 (p, J=7.3 Hz, 2H); MS (ESI(+)) m/e 400 (M+H)+.

Workup

  1. customto give a precipitate which
  2. filtrationwas filtered
  3. washwashed with cold ethyl acetate
  4. dry with materialether and dried under vacuum

Sources & evidence

ORD record
ord-dcabe76a08ff4a809e3c32cb6b07d4b3
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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