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3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole-5-carbonitrile → (3-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl)methanamine

HRID 2223795
Notes
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Reaction equation

HRID 2223795 reaction equation
[CH3:1][N:2]1[CH2:7][CH:6]=[C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][N:2]1[CH2:3][CH:4]=[C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][NH2:18])[CH:15]=3)[NH:10][CH:9]=2)[CH2:6][CH2:7]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 149732163-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole-5-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 57474448(3-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl)methanamineYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To an argon purged round bottom flask fitted with a condenser and magnetic stirbar containing 49 (105 mg, 0.442 mmol) was added lithium aluminum hydride (34 mg, 0.896 mmol) followed by absolute THF (5 mL). A small amount of gas was produced. Once no more bubbling occurred, the reaction was transferred to an oil bath heated to 75° C. The reaction was stirred at this temperature for 18 hrs. The reaction was then cooled to room temperature. The reaction was quenched with water (0.1 mL), 3N NaOH (0.1 mL) and water (0.3 mL) sequentially, followed by filtration through a celite plug. The plug was washed with THF and the filtrate concentrated to afford a yellow oil, compound 50 (106 mg, 99%). 1H NMR (DMSO) δ 10.95 (br s, NH), 7.74 (s, 1H), 7.32-7.31 (d, J=2.4 Hz, 1H), 7.30-7.27 (d, J=8.4 Hz, 1H), 7.08-7.05 (d, J=8.1 Hz, 1H), 6.14 (s, 1H), 3.77 (s, 2H), 3.29 (s, 2H), 3.06-3.05 (d, J=2.7 Hz, 2H), 2.57-2.56 (d, J=4.5 Hz, 2H), 2.51-2.50 (d, J=1.2 Hz, 2H), 2.29 (s, 3H), 1.75 (br s, 2NH).

Workup

  1. customTo an argon purged round bottom flask fitted with a condenser
  2. customA small amount of gas was produced
  3. customOnce no more bubbling
  4. customthe reaction was transferred to an oil bath
  5. temperatureThe reaction was then cooled to room temperature
  6. customThe reaction was quenched with water (0.1 mL), 3N NaOH (0.1 mL) and water (0.3 mL) sequentially
  7. filtrationfollowed by filtration through a celite plug
  8. washThe plug was washed with THF
  9. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-01ff1eb361f74b959a5d0d805fb2917f
Source dataset
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07375219B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes