Hydrazine, 1,1-diphenyl-, hydrochloride (1:1) → 5-Phenyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indole-2-carboxylic acid tert-butyl ester

HRID 269959Notes

Reaction equation

Cl.[C:2]1([N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)N)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]>N1C=CC=CC=1>[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][C:26]2[N:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[C:25]=2[CH2:24]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 1,1-diphenylhydrazine hydrochloride (0.365 g, 1.65 mmol) and 4-oxo-1-piperidinecarboxylic acid tert-butyl ester (0.329 g, 1.65 mmol) in pyridine (3 mL) was heated in a sealed tube at 120° C. with stirring for 3 h. The reaction mixture was subsequently cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was separated, dried (MgSO4), filtered and evaporated to dryness. The residue was chromatographed (SiO2/hexanes:ethyl acetate, 3:2) to give the title compound (0.214 g, 37%) as a brown oil. 1H NMR (400 MHz, CDCl3) δ 7.51 (m, 2H), 7.40 (m, 1H), 7.35 (m, 2H), 7.26 (m, 2H), 7.14 (m, 2H), 4.72 (s, 2H), 3.78 (s, 2H), 2.71 (s, 2H), 1.51 (s, 9H); LCMS: m/e 349 (M+H)+.

Workup

temperatureThe reaction mixture was subsequently cooled to room temperature
custompartitioned between ethyl acetate and water
customThe organic layer was separated
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated to dryness
customThe residue was chromatographed (SiO2/hexanes:ethyl acetate, 3:2)

Sources & evidence

ORD record: ord-8a3392c05c1a4c6b80fc2f6449ae3185
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07449476B2

Reaction notes

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