Water → 3-Methyl-5-(2-piperidin-1-yl-ethyl)-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one

HRID 2365016Notes

Reaction equation

HRID 2365016 reaction equation
C([O:3][C:4]([C:6]1[C:10]([CH3:11])=[CH:9][NH:8][C:7]=1[CH2:12][CH2:13][NH:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=O)C.C[Al](C)C.O.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:11][C:10]1[C:6]2[C:4](=[O:3])[N:14]([CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:13][CH2:12][C:7]=2[NH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 16682925TrimethylaluminumHCID 666076814-methyl-2-[2-(2-piperidin-1-yl-ethylamino)-ethyl]-1H-pyrrole-3-carboxylic acid ethyl ester

Product 1

HCID 666084063-Methyl-5-(2-piperidin-1-yl-ethyl)-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-oneYield 87.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A stirred solution of 4-methyl-2-[2-(2-piperidin-1-yl-ethylamino)-ethyl]-1H-pyrrole-3-carb oxylic acid ethyl ester (3.07 g, 10 mmol) in toluene (50 ml) was added dropwise slowly with 2M trimethyl aluminum in toluene (10 ml, 20 mmol) under an argon atmosphere. The mixture was stirred for 1 hour at room temperature and heated to reflux for another 4 hours. The reaction mixture was cooled down to 0° C. in ice/water bath, added with cold water (50 ml) and stirred for 5 minutes. The mixture was adjusted to pH12 with 10% aqueous sodium hydroxide solution and extracted with dichloromethane (40 ml×3). The combined organic extracts were washed with brine (15 ml), filtered through a pad of Celite. The filtrate was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 3-methyl-5-(2-piperidin-1-yl-ethyl)-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one (2.29 g) as a red oil which was used as such.

Workup

  1. temperatureheated
  2. temperatureto reflux for another 4 hours
  3. stirringstirred for 5 minutes
  4. extractionextracted with dichloromethane (40 ml×3)
  5. washThe combined organic extracts were washed with brine (15 ml)
  6. filtrationfiltered through a pad of Celite
  7. dry with materialThe filtrate was dried with anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5f8f3ee8716c4494aa9536f323b4e1dc
Source dataset
uspto-grants-2014_04
Patent number
US08697692B2

Reaction notes

Loading…