N,N-Dimethylglycine → N-(2-(2,5-Dimethyl-1-pyrrolyl)ethyl)-(N,N-dimethylamino)acetamide

HRID 1904229Notes

Reaction equation

HRID 1904229 reaction equation
[CH3:1][N:2]([CH2:4][C:5]([OH:7])=O)[CH3:3].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:20][CH2:21][CH2:22][N:23]1[C:27]([CH3:28])=[CH:26][CH:25]=[C:24]1[CH3:29]>COCCOC>[CH3:29][C:24]1[N:23]([CH2:22][CH2:21][NH:20][C:5](=[O:7])[CH2:4][N:2]([CH3:3])[CH3:1])[C:27]([CH3:28])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 673N,N-DimethylglycineHCID 682631,1'-CarbonyldiimidazoleHCID 137700502-(2,5-Dimethyl-1H-pyrrol-1-yl)ethan-1-amine

Product 1

HCID 13770064N-(2-(2,5-Dimethyl-1-pyrrolyl)ethyl)-(N,N-dimethylamino)acetamide

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

5.2 g (0.05 mol) of N,N-dimethylaminoacetic acid and 8.1 g (0.05 mol) of carbonyldiimidazole in 20 ml of ethylene glycol dimethyl ether are stirred at 70° C. for 15 min. After addition of 5.5 g (0.04 mol) of 1-(2-aminoethyl)-2,5-dimethylpyrrole, dissolved in 20 ml of ethylene glycol dimethyl ether, to the mixture it is stirred at room temperature for 5 h, then concentrated, water is added, and the mixture is extracted first when acid and then when alkaline. The product contained in the extract from the mixture which has been made alkaline is crystallized using ligroin. Yield: 4.3 g (39% of theory), Melting point: 63°-65° C. Elemental analysis: C12H21N3O (223.32) calculated: C 64.5 H 9.5 N 18.8 O 7.2 found: C 64.0 H 9.4 N 18.5 O 8.0

Workup

  1. concentrationconcentrated
  2. additionwater is added
  3. extractionthe mixture is extracted first when acid
  4. extractionextract from the mixture which
  5. customis crystallized

Sources & evidence

ORD record
ord-732bc9f7c96643e3aa7eb9ec59007b2f
Source dataset
uspto-grants-1989_06
Patent number
US04837225

Reaction notes

Loading…