Ethanolamine → 1-(3,4-Dihydro-2H-pyrano[2,3-b]pyridin-2-yl)methanamine

HRID 1655281Notes

Reaction equation

HRID 1655281 reaction equation
C1(=O)[N:5]([CH2:6][CH:7]2[O:16][C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[CH2:9][CH2:8]2)C(=O)C2=CC=CC=C12.NCCO>>[NH2:5][CH2:6][CH:7]1[O:16][C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[CH2:9][CH2:8]1

Participants

3

Reactant 2

HCID 700EthanolamineHCID 19791571HCID 19791571, compound

Product 1

HCID 197915651-(3,4-Dihydro-2H-pyrano[2,3-b]pyridin-2-yl)methanamineYield 94.1%

Procedure

3.2 g (11 mmol) of the compound from Example VII and 9.2 g (150 mmol) of 2-aminoethanol are heated under nitrogen to 80° C. After 5 minutes the mixture is cooled, and the reaction mixture is partitioned between 70 ml of toluene and 92 ml of 5% strength NaCl solution. The phases are separated, and the aqueous phase is extracted with dichloromethane. The combined organic phases are dried and evaporated in vacuo. 1.7 g of the title compound are obtained as a light yellow oil.

Workup

  1. temperatureAfter 5 minutes the mixture is cooled
  2. customthe reaction mixture is partitioned between 70 ml of toluene and 92 ml of 5% strength NaCl solution
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted with dichloromethane
  5. customThe combined organic phases are dried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-471e2a5674f843d88b89dfb159dcf82c
Source dataset
uspto-grants-1993_10
Patent number
US05250540

Reaction notes

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