Hydrochloric Acid → 2-methyl-2,3,4,5-tetrahydro-1H-pyrido(4,3-b)indole

HRID 526298Notes

Reaction equation

[C:1]1([NH:7]N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:10][N:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1.[OH-].[Na+].[Na+].[Cl-]>O>[CH3:10][N:11]1[CH2:16][CH2:15][C:14]2[NH:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=3[C:13]=2[CH2:12]1

Participants

Conditions

Temperature: 55 °C

Procedure

To a suspension of phenylhydrazine (5.4 g) in 75 mL water was added slowly 4.2 mL of 12 N HCl, followed by addition of 1-methylpiperidin-4-one (6.7 g). Additional 16 g of 12N HCl was added and the reaction mixture was heated at 55° C. for 2 days. After cooling in a ice-water bath, 10 N NaOH solution was added slowly until pH>12.20 g of NaCl was added to the mixture and the reaction mixture was extracted with 2×100 mL of CH2Cl2. The combined extracts were dried over Na2SO4, filtered and concentrated. The residue was swished from EtOAc to give 7 g of the title compounds as a light yellow solid.

Workup

temperatureAfter cooling in a ice-water bath
additionwas added to the mixture
extractionthe reaction mixture was extracted with 2×100 mL of CH2Cl2
dry with materialThe combined extracts were dried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-fb496266fd78489d96191e36c8b31edb
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09345905B2

Reaction notes

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