Dimethylamine → HCID 9794514, compound

HRID 1636372Notes

Reaction equation

HRID 1636372 reaction equation
[OH:1][CH:2]([C:6]1[CH:7]=[CH:8][C:9]([C:12]([O:14]C)=O)=[N:10][CH:11]=1)[CH:3]([OH:5])[CH3:4].[CH3:16][NH:17][CH3:18].CO>>[OH:1][CH:2]([C:6]1[CH:7]=[CH:8][C:9]([C:12]([N:17]([CH3:18])[CH3:16])=[O:14])=[N:10][CH:11]=1)[CH:3]([OH:5])[CH3:4]

Participants

4

Reactant 3

HCID 674DimethylamineHCID 887MethanolHCID 9859160HCID 9859160, compound

Product 1

HCID 9794514HCID 9794514, compoundYield 80.6%

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 5-(1,2-dihydroxypropyl)-2-pyridinecarboxylate (52.0 mg, 0.25 mmol) and a 2.0M solution of dimethylamine in methanol (Aldrich, 15.0 ml, 30.0 mmol) was stirred and heated at a bath temperature of 100° C. in a microreactor for four nights. After cooling, the reaction mixture was concentrated in vacuo. The residue (60.3 mg) was purified by preparative TLC [Merck Kieselgel 60, Art 1.05744, 0.5 mm thick, x2; development: CH2Cl2 --MeOH (8:1); elution: CH2Cl2 --MOH (3:1), 240 ml]. The recovered white solid residue was suspended in THF, and the mixture was filtered through a short pad of Celite. The filter cake was washed with THF. The combined filtrate and washings were concentrated in vacuo to give 5-(1,2-dihydroxypropyl)-N,N-dimethyl-2-pyridinecarboxamide as a white solid (45.2 mg, 80.6%): 1H-NMR (270 MHz) δ(CDCl3): 8.41 (d, J=1.8 Hz, 1H), 7.76 (dd, J=7.9, 1.8 Hz, 1H), 7.52 (d, J=7.9 Hz, 1H), 4.86 (d, J=3.7 Hz, 1H), 4.11~3.97 (m, 1H), 3.80 (br.s, 1H), 3.13 (s, 3H), 3.04 (s, 3H), 2.68 (br.s, 1H), 1.15 (d, J=6.6 Hz, 3H) ppm; MS m/z: 225 (7.9%, M+ +1), 224 (50.9%, M+), 153 (100%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customThe residue (60.3 mg) was purified by preparative TLC [Merck Kieselgel 60, Art 1.05744, 0.5 mm thick, x2; development: CH2Cl2 --MeOH (8:1); elution: CH2Cl2 --MOH (3:1), 240 ml]
  4. filtrationthe mixture was filtered through a short pad of Celite
  5. washThe filter cake was washed with THF
  6. concentrationThe combined filtrate and washings were concentrated in vacuo

Sources & evidence

ORD record
ord-d7619b9e5cb34175ab4dcf89a2249500
Source dataset
uspto-grants-2000_03
Patent number
US06034107

Reaction notes

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