3-Bromothiophene → 1-(9,10-Dihydro-9,10-methanoanthracen-9-ylmethyl)-4-(3-thienyl)piperidin-4-ol

HRID 1721769Notes

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.Br[C:25]1[CH:29]=[CH:28][S:27][CH:26]=1>>[CH:11]1[C:12]2[C:13]3([CH2:16][N:17]4[CH2:22][CH2:21][C:20]([C:25]5[CH:29]=[CH:28][S:27][CH:26]=5)([OH:23])[CH2:19][CH2:18]4)[CH2:15][CH:6]([C:5]4[C:14]3=[CH:1][CH:2]=[CH:3][CH:4]=4)[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

Reactant 2

HCID 133833-Bromothiophene

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

Product 1

HCID 214807071-(9,10-Dihydro-9,10-methanoanthracen-9-ylmethyl)-4-(3-thienyl)piperidin-4-olYield 81%

Procedure

Using a procedure similar to that described in example 1 except starting with 1-(9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)-4-piperidinone (described in example 5d) and employing 3-bromothiophene, the title compound was formed in 81% yield as an off-white solid, mp 273°-277° C. (dec). free base: 1H NMR (CDCl3, 250 MHz) 7.17 (m, 7H), 6.94 (m, 4H), 4.26 (s, 1H), 3.46 (s, 1H), 2.84 (m, 2H), 2.71 (m, 2H), 2.60 (d, J=1.4 Hz, 2H), 2.12 (m, 2H), 1.83 (m, 2H) MS (CI, CH4) m/z 388 (M+1,100), 416 (M+29,20), 370 (51), 304 (10), 196 (12) hydrochloride salt:

Sources & evidence

ORD record: ord-dd7cf6ed51264f33bb41a38396837bca
Source dataset: uspto-grants-1996_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05512575

Reaction notes

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