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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-acetoxy-N-(1-methyl-1-phenylethyl)benzamide

HRID 21082
Notes
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Reaction equation

HRID 21082 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=O)(=[O:3])[CH3:2].CCN=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O.[C:36]([NH2:45])([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([CH3:38])[CH3:37]>CN(C=O)C>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([NH:45][C:36]([CH3:38])([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH3:37])=[O:10])(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 68509CumylamineHCID 2386693-Acetoxybenzoic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 684903353-acetoxy-N-(1-methyl-1-phenylethyl)benzamideYield 73.1%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

In a similar manner to Step 1 of Example 137, 3-acetoxybenzoic acid (7.92 g, 44.0 mmol) was dissolved in DMF (45 mL), and the solution was treated with EDCI (12.7 g, 66.0 mmol), HOBT monohydrate (3.37 g, 22.0 mmol) and cumylamine (14.2 mL, 96.8 mmol), followed by purification by slurry using diisopropylether to obtain 3-acetoxy-N-(1-methyl-1-phenylethyl)benzamide (9.57 g, yield 73%).

Workup

  1. customfollowed by purification by slurry

Sources & evidence

ORD record
ord-6a266b339e5f434a9f12acc5d0d1df8d
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07745641B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes