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1-Pyrrolidineethanamine → 3-bromo-N-[2-(pyrrolidin-1-yl)ethyl]benzamide

HRID 9772
Notes
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Reaction equation

HRID 9772 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][CH2:5]1.P(C#N)(OCC)(OCC)=O.C(N(CC)CC)C.[Br:26][C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=1)[C:30](O)=[O:31]>CN(C)C=O.O>[Br:26][C:27]1[CH:28]=[C:29]([C:30]([NH:1][CH2:2][CH2:3][N:4]2[CH2:8][CH2:7][CH2:6][CH2:5]2)=[O:31])[CH:33]=[CH:34][CH:35]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 13441-PyrrolidineethanamineHCID 8471TriethylamineHCID 114563-Bromobenzoic acidHCID 76257Diethyl cyanophosphonate

Product 1

HCID 8486853-bromo-N-[2-(pyrrolidin-1-yl)ethyl]benzamideYield 85.4%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Procedure

1-(2-Aminoethyl)pyrrolidine (4.34 g), diethyl cyanophosphate (5.57 ml) and triethylamine (10.4 ml) were added to a solution of 3-bromobenzoic acid (5.00 g) in N,N-dimethylformamide (DMF; 60 ml), and the mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with water and then extracted with diethyl ether. The extract was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residues were crystallized from hexane to give the title compound (6.31 g).

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residues were crystallized from hexane

Sources & evidence

ORD record
ord-20bfb9c6c3334504a550ae3aff9a8c0e
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091247B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes