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Dimethylamine → (Rac)-2,5-dibromo-n,n-dimethyl-pentanamide

HRID 1096187
Notes
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Reaction equation

HRID 1096187 reaction equation
[CH3:1][NH:2][CH3:3].CCN(CC)CC.[Br:11][CH:12]([CH2:16][CH2:17][CH2:18][Br:19])[C:13](Cl)=[O:14]>C(Cl)Cl>[Br:11][CH:12]([CH2:16][CH2:17][CH2:18][Br:19])[C:13]([N:2]([CH3:3])[CH3:1])=[O:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8471TriethylamineHCID 111850322,5-Dibromopentanoyl chloride

Product 1

HCID 20370625(Rac)-2,5-dibromo-n,n-dimethyl-pentanamideYield 64.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of dimethylamine (0.91 ml, 7.18 mmol; 40% solution in water) and 2.75 ml (19.76 mmol) of Et3N in 6 ml of CH2Cl2 cooled at 0° C. was added dropwise a solution of 2,5-dibromo-pentanoyl chloride (1.00 g, 3.59 mmol) in 4 ml CH2Cl2. After stirring 1 h at RT, the reaction mixture was partitioned between CH2Cl2 and water. The organic phases were washed with water and brine and the aqueous layers extracted twice with CH2Cl2. The organic phases were dried over MgSO4, evaporated and purified by flash silica gel column (EtOAc/n-heptane 1:1) to afford 0.66 g (64%) of the title product as light yellow oil. MS: 288.1 (2Br, MH+).

Workup

  1. customthe reaction mixture was partitioned between CH2Cl2 and water
  2. washThe organic phases were washed with water and brine
  3. extractionthe aqueous layers extracted twice with CH2Cl2
  4. dry with materialThe organic phases were dried over MgSO4
  5. customevaporated
  6. custompurified by flash silica gel column (EtOAc/n-heptane 1:1)

Sources & evidence

ORD record
ord-a2abdc35666f4c099e4b246f947d317e
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08138175B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes