1-Indanone → Piperidine

HRID 1460349Notes

Reaction equation

HRID 1460349 reaction equation
N1C=CC=[C:3]2[C:7](=[O:14])[C:8]3[C:13]([C:2]=12)=[CH:12][CH:11]=[CH:10][CH:9]=3.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]2CC3C([C:16]=12)=CC=CC=3.[C:28]1(=[O:37])[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30][CH2:29]1.ClC1C=C2C(CC[C:45]2=[O:48])=CC=1CC1CCCC1>C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:45][O:48][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][C:10]=1[O:37][CH3:28])[C:7](=[O:14])[CH2:3][CH2:2]2.[CH3:7][O:14][C:34]1[CH:35]=[C:36]2[C:31]([CH2:30][CH2:29][C:28]2=[O:37])=[CH:32][CH:33]=1.[NH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

8

Reactant 4

HCID 67351-IndanoneHCID 92054-AzafluoreneHCID 774895H-Indeno(1,2-b)pyridin-5-oneHCID 19874650HCID 19874650, compound

Product 3

HCID 8082PiperidineHCID 750185,6-Dimethoxy-1-indanoneHCID 3340366-Methoxy-1-Indanone

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

Synthesis substrates 5H-indeno[1,2-b]pyridin-5-one and 5H-indeno[1,2-b]pyridine (as 4-azafluorene from Aldrich Chemical, Inc.) and their derivatives are prepared according to a general procedure of Parcell and Hauck, J. Org. Chem., 21, 3468 (1963), wherein the piperidineenamine of 2,3-dihydro-1H-inden-1-one (available from Aldrich Chemical, Inc.) --4,--5 or --6-chloro or fluoro-2,3-dihydro-1H-inden-1-one (Oliver and Marechal, Bull. Soc. Chim. France, (1973), 3092), 6-chloro-5-cyclopentylmethyl-2,3-dihydro-1H-inden-1-one (Biere et al., Eur. J. Med., 18, 255 (1983), 5,6-dimethoxy-2,3-dihydro-1H-inden-1-one (Koo, J. Amer. Chem. Soc., 75, 1891 (1953)), 5 or 6-methoxy-2,3-dihydro-1H-inden-1-one (available from Aldrich Chemical, Inc.,) or other substituted 1-indanones is formed from piperidine in the presence of p-toluenesulfonic acid catalyst according to the procedure of Heyl and Herr, J. Amer. Chem. Soc., 75, 1918 (1953). The resulting piperidineenamine is reacted with 3-bromopropylamine hydrobromide or hydrochloride (available from Aldrich Chemical, Inc.) to yield an imine product.

Workup

  1. customare prepared

Sources & evidence

ORD record
ord-257580fb2cb14ae2b47bb1e19ec75256
Source dataset
uspto-grants-1991_12
Patent number
US05070100

Reaction notes

Loading…