2-(Dimethylamino)ethanol → HCID 67974124, compound

HRID 706606Notes

Reaction equation

HRID 706606 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].[Na].Cl[C:9]1[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=1>>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][O:5][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=1

Participants

4

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 5818662-Amino-4-chloropyridineHCID 5360545Sodium

Product 1

HCID 67974124HCID 67974124, compoundYield 537.6%

Procedure

2-Dimethylaminoethanol (34.8 g, 39.0 mmol) was treated with sodium (2.7 g, 11.7 mmol) in a sealed tube and stirred at ambient temperature until homogeneous. 4-Chloropyridin-2-amine (5 g, 3.9 mmol) was added and reaction heated to 150° C. and stirred in sealed tube for 8 hours. The mixture was cooled to ambient temperature before concentrating and triturating with dichloromethane (50 mL) four times. The combined triturates were concentrated and purified by column chromatography to give 4-(2-(dimethylamino)ethoxy)pyridin-2-amine as a yellow solid (3.8 g).

Workup

  1. customreaction
  2. temperatureheated to 150° C.
  3. stirringstirred in sealed tube for 8 hours
  4. temperatureThe mixture was cooled to ambient temperature
  5. concentrationbefore concentrating
  6. customtriturating with dichloromethane (50 mL) four times
  7. concentrationThe combined triturates were concentrated
  8. custompurified by column chromatography

Sources & evidence

ORD record
ord-50cbd6d898c24ce6b787cc69eba0530f
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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