4-(4-Chlorophenyl)-4-hydroxypiperidine → 1-(2-Chloro-9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)-4-(4-chlorophenyl)piperidin-4-ol

HRID 1721775Notes

Reaction equation

HRID 1721775 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[CH:12]3[CH2:16][C:5]([CH:17]=O)([C:6]4[C:11]3=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:4]=2[CH:3]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2([OH:32])[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:22][CH:21]=1>>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[CH:12]3[CH2:16][C:5]([CH2:17][N:29]4[CH2:28][CH2:27][C:26]([C:23]5[CH:24]=[CH:25][C:20]([Cl:19])=[CH:21][CH:22]=5)([OH:32])[CH2:31][CH2:30]4)([C:6]4[C:11]3=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 196986392-Chloro-9-formyl-9,10-dihydro-9,10-methanoanthracene

Product 1

HCID 214805801-(2-Chloro-9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)-4-(4-chlorophenyl)piperidin-4-olYield 29%

Procedure

Using a procedure similar to that described in example 21 except starting with 2-chloro-9-formyl-9,10-dihydro-9,10-methanoanthracene (described in example 1i) and 4-(4-chlorophenyl)-4hydroxypiperidine, the title compound hydrochloride salt was obtained in 29% yield as a white powder, mp 261°-263° C. elemental

Sources & evidence

ORD record
ord-6c71aa2c4d2c49e5bd971bf289c7f286
Source dataset
uspto-grants-1996_04
Patent number
US05512575

Reaction notes

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