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1-Pentanol → 6-chloro-2,3-dihydro-2-[1-[(2-methylphenyl)methyl]-4-piperidinyl]-1,3-dioxo-1H-isoindole-5-sulfonamide

HRID 745834
Notes
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Reaction equation

HRID 745834 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[NH:8][C:6](=[O:7])[C:5]2=[CH:11][C:12]=1[S:13](=[O:16])(=[O:15])[NH2:14].N[CH:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:31])[CH2:20][CH2:19]1.C(O)CCCC.O=C1C2C(=CC=CC=2)C(=O)N1>CCCCCCC>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([C:6](=[O:7])[N:8]([CH:18]3[CH2:19][CH2:20][N:21]([CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[CH3:31])[CH2:22][CH2:23]3)[C:9]2=[O:10])=[CH:11][C:12]=1[S:13]([NH2:14])(=[O:16])=[O:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 62761-PentanolHCID 6809PhthalimideHCID 197334-(Aminosulfonyl)-5-chlorophthalimideHCID 126418341-[(2-Methylphenyl)methyl]piperidin-4-amine

Product 1

HCID 133706076-chloro-2,3-dihydro-2-[1-[(2-methylphenyl)methyl]-4-piperidinyl]-1,3-dioxo-1H-isoindole-5-sulfonamide

Reagents, catalysts & solvents 1

HCID 8900
Heptane
Solvent

Procedure

A mixture of 4-chloro-5-sulfamoylphthalimide (5.74 g., 0.022 mole) and 4-amino-1-[(2-methylphenyl)methyl]piperidine (4.5 g., 0.022 mole) in 85 ml. of n-pentanol was reacted according to the procedure of Example 1(a). Addition of n-heptane to the reaction mixture afforded 7.9 g. (80%) of the 1,3-dioxoisoindole product, m.p. 283°-243°. Crystallization of this material from DMF-methanol provided analytically pure 6-chloro-2,3-dihydro-2-[1-[(2-methylphenyl)methyl]-4-piperidinyl]-1,3-dioxo-1H-isoindole-5-sulfonamide, m.p. 244°-245° (dec.).

Workup

  1. customafforded 7.9 g
  2. customCrystallization of this material from DMF-methanol

Sources & evidence

ORD record
ord-aa54ee27ac754616ae29fd99a2216abc
Source dataset
uspto-grants-1986_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04600758

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes