(9,10-Dihydro-9,10-methanoanthracen-9-ylmethyl)-4-piperidinone → 4-Butyl-1-(9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)piperidin-4-ol

HRID 1721785Notes

Reaction equation

[CH:1]1[C:14]2[C:13]3([CH2:16][N:17]4[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]4)[CH2:15][CH:6]([C:7]4[C:12]3=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:24]([Li])[CH2:25][CH2:26][CH3:27]>>[CH2:24]([C:20]1([OH:23])[CH2:21][CH2:22][N:17]([CH2:16][C:13]23[CH2:15][CH:6]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=42)[C:5]2[C:14]3=[CH:1][CH:2]=[CH:3][CH:4]=2)[CH2:18][CH2:19]1)[CH2:25][CH2:26][CH3:27]

Participants

Reactant 2

HCID 21480605(9,10-Dihydro-9,10-methanoanthracen-9-ylmethyl)-4-piperidinone

HCID 178418339Butyllithium

Product 1

HCID 214805864-Butyl-1-(9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)piperidin-4-ol

Procedure

Using a procedure similar to that described in example 49 except starting with 1-(9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)-4-piperidinone (described in example 5d) and employing n-butyllithium, the title compound was formed as a white solid, mp 194°-196° C. TLC analysis on the free base (Rf 0.22, 30% ethyl acetate in hexane). free base: 1H NMR (CDCl3, 250 MHz) 7.20 (m, 4H), 6.94 (m, 4H), 4.26 (s, 1H), 3.41 (s, 2H), 2.73 (m, 2H), 2.60 (d, J=2.0 Hz, 2H), 1.53 (m, 10H), 0.9 (t, 3H) MS (CI, CH4) m/z 362 (M+1,100), 390 (M+29,13), 344 (47), 304 (44) hydrochloride salt:

Sources & evidence

ORD record: ord-35de9ced9ec44ef6893b99b43b46f30f
Source dataset: uspto-grants-1996_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05512575

Reaction notes

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