Triethylamine → HCID 58171579, compound

HRID 1752297Notes

Reaction equation

HRID 1752297 reaction equation
C([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][N:14]=2)[CH2:9]1)C1C=CC=CC=1.CCN(CC)CC.C(Cl)(=O)OC(Cl)C>C(Cl)Cl>[CH3:19][C:16]1[CH:17]=[CH:18][C:13]([CH:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)=[N:14][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5213051-Chloroethyl chloroformateHCID 58171488HCID 58171488, compound

Product 1

HCID 58171579HCID 58171579, compoundYield 117%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-(1-benzylpyrrolidin-3-yl)-5-methylpyridine (200 mg, 0.79 mmol) in dry CH2Cl2 (3 mL) were added Et3N (80 mg, 0.79 mmol) and 1-chloroethyl carbonochloridate (225 mg, 1.6 mmol) at 0° C. The mixture was stirred at 0° C. for 2 h. The reaction mixture was concentrated under vacuum and dissolved in CH2Cl2 (5 mL). The organic solution was washed with water (20 mL×3), and the combined aqueous layers were concentrated to give crude 5-methyl-2-(pyrrolidin-3-yl)pyridine (150 mg, 82%) as a solid, which was used for next step without purification.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutiondissolved in CH2Cl2 (5 mL)
  3. washThe organic solution was washed with water (20 mL×3)
  4. concentrationthe combined aqueous layers were concentrated

Sources & evidence

ORD record
ord-e9764086681948ea88e3bb0f93f4f572
Source dataset
uspto-grants-2015_10
Patent number
US09163012B2

Reaction notes

Loading…