Diisopropylethylamine → HCID 117830954, compound

HRID 515928Notes

Reaction equation

HRID 515928 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]([OH:9])=O)=[C:3]1[CH3:10].ClC(N(C)C)=C(C)C.[CH2:19]([O:26][C:27]1[CH:34]=[CH:33][C:30]([NH:31][CH3:32])=[CH:29][CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(C(C)C)C(C)C)C>ClCCCl.ClCCl>[CH2:19]([O:26][C:27]1[CH:28]=[CH:29][C:30]([N:31]([CH3:32])[C:7]([C:4]2[CH:5]=[CH:6][N:2]([CH3:1])[C:3]=2[CH3:10])=[O:9])=[CH:33][CH:34]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 162176454-(Benzyloxy)-N-methylanilineHCID 225617641,2-Dimethyl-1H-pyrrole-3-carboxylic acid

Product 1

HCID 117830954HCID 117830954, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1,2-dimethylpyrrole-3-carboxylic acid (2.085 g; 15 mmol) in 1,2-dichloroethane (40 mL) there is added 1-chloro-N,N,2-trimethyl-prop-1-en-1-amine (2.37 mL; 17.9 mmol), and the solution formed is stirred for 1 hour. To the resulting solution there is added, dropwise, an ice-cold solution of 4-benzyloxy-N-methyl-aniline (3.73 g; 15 mmol) and N-ethyl-N-isopropyl-propan-2-amine (7.75 mL; 45 mmol) in 1,2-dichloroethane (40 mL). The reaction mixture is stirred at ambient temperature for 1 hour; it is then diluted with dichloromethane (250 mL) and washed with water (2×30 mL), dried over Na2SO4 and evaporated. The crude product is triturated with diethyl ether and the solid formed is filtered off to yield the title compound.

Workup

  1. customthe solution formed
  2. additionTo the resulting solution there is added
  3. stirringThe reaction mixture is stirred at ambient temperature for 1 hour
  4. washwashed with water (2×30 mL)
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe crude product is triturated with diethyl ether
  8. customthe solid formed
  9. filtrationis filtered off

Sources & evidence

ORD record
ord-33abba4a03ed46dabb45d2584086f89f
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

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