Dimethylamine → 2-Carboxy-4-methyl-2-[(dimethylamino)methyl]pentanoic acid

HRID 444192

Reaction equation

HRID 444192 reaction equation
[C:1]([CH:4]([CH2:8][CH:9]([CH3:11])[CH3:10])[C:5]([OH:7])=[O:6])([OH:3])=[O:2].[CH3:12][NH:13][CH3:14].[CH2:15]=O>O>[C:5]([C:4]([CH2:12][N:13]([CH3:15])[CH3:14])([CH2:8][CH:9]([CH3:11])[CH3:10])[C:1]([OH:3])=[O:2])([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 78069Isobutylmalonic acid

Product 1

HCID 130175562-Carboxy-4-methyl-2-[(dimethylamino)methyl]pentanoic acidYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

2-Carboxy-4-methylpentanoic acid (67 g) is suspended in 400 ml of water and cooled to 5° C. Aqueous 40% dimethylamine (50 g) is added to the suspension followed by aqueous 37% formaldehyde (35.7 g). The resulting solution is stirred for about 16 hours and solid product is filtered and dried in vacuo to yield 57.3 g of the title compound, melting point 134°-137° C. with carbon dioxide and dimethylamine given off.

Workup

  1. filtrationsolid product is filtered
  2. customdried in vacuo

Sources & evidence

ORD record
ord-1764e36943b84ecdaed90320f5ae4ed7
Source dataset
uspto-grants-1981_04
Patent number
US04263293

Linked notes

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