Water → HCID 55285635, compound

HRID 19737Notes

Reaction equation

HRID 19737 reaction equation
[N:1]1[C:9]2[CH2:8][CH:7]([C:10]([NH2:12])=O)[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[N:1]1[C:9]2[CH2:8][CH:7]([CH2:10][NH2:12])[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 45084613HCID 45084613, compound

Product 1

HCID 55285635HCID 55285635, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6,7-Dihydro-5H-[1]pyrindine-6-carboxylic acid amide (0.209 g, 1.28 mmol) is added portionwise to a suspension of LiAlH4 (0.204 g, 5.38 mmol) in THF (10 ml). After 5 minutes at ambient temperature, the reaction is heated to reflux for 1.5 hours and then cooled. Water (0.2 ml) is cautiously added, followed by 15% aqueous sodium hydroxide (0.2 ml), followed by further water (0.6 ml). The resultant granular precipitate is filtered and washed with EtOAc. The combined filtrate and washings are evaporated to afford C-(6,7-dihydro-5H-[1]pyrindin-6-yl)methylamine. δc 35.2 (t), 38.9 (t), 41.0 (d), 47.6 (t), 121.6 (d), 132.6 (d), 136.4 (s), 148.1 (s), 164.8 (s).

Workup

  1. temperaturethe reaction is heated
  2. temperatureto reflux for 1.5 hours
  3. temperaturecooled
  4. filtrationThe resultant granular precipitate is filtered
  5. washwashed with EtOAc
  6. customThe combined filtrate and washings are evaporated

Sources & evidence

ORD record
ord-ac4262e8f9374541be32b7d29dadbb06
Source dataset
uspto-grants-2010_06
Patent number
US07745462B2

Reaction notes

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