4-(4-Methylbenzyl)-piperidin-4-ol → (RS)-1-(5-benzyloxy-2,3-dihydro-benzofuran-2-ylmethyl)-4-(4-methyl-benzyl)-piperidin-4-ol

HRID 278420Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][CH:15]([CH2:17]Br)[CH2:14][C:13]=2[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][C:21]1[CH:34]=[CH:33][C:24]([CH2:25][C:26]2([OH:32])[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:23][CH:22]=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][CH:15]([CH2:17][N:29]3[CH2:30][CH2:31][C:26]([CH2:25][C:24]4[CH:23]=[CH:22][C:21]([CH3:20])=[CH:34][CH:33]=4)([OH:32])[CH2:27][CH2:28]3)[CH2:14][C:13]=2[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

(RS)-5-Benzyloxy-2-bromomethyl-2,3-dihydro-benzofuran (840 mg, 2.63 mmol) and 4-(4-methyl-benzyl)-piperidin-4-ol (1.08 g, 5.26 mmol) were suspended in toluene (20 ml) and heated to 110° C. for 17 hr. The mixture was filtered and evaporated to afford an orange oil which was chromatographed over SiO2 (Merck 230-400 mesh) with MeOH—CH2Cl2 (3:97) to afford (RS)-1-(5-benzyloxy-2,3-dihydro-benzofuran-2-ylmethyl)-4-(4-methyl-benzyl)-piperidin-4-ol as a yellow oil (1.03 g, 2.32 mmol, 88%), MS: m/e=444.5 (M+H+).

Workup

filtrationThe mixture was filtered
customevaporated
customto afford an orange oil which
customwas chromatographed over SiO2 (Merck 230-400 mesh) with MeOH—CH2Cl2 (3:97)

Sources & evidence

ORD record: ord-dd063d9b45304748a78fbcd9104b9dea
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06359138B1

Reaction notes

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