Picolyl chloride hydrochloride → 1-(4-Methoxyphenyl)-4-(2,2,4,6,7-pentamethyl-3-(2-pyridylmethyl)oxy-2,3-dihydro-1-benzofuran-5-yl)piperazine

HRID 1272323Notes

Reaction equation

HRID 1272323 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[C:25]([CH3:38])=[C:26]([CH3:37])[C:27]4[O:31][C:30]([CH3:33])([CH3:32])[CH:29]([OH:34])[C:28]=4[C:35]=3[CH3:36])[CH2:20][CH2:19]2)=[CH:14][CH:13]=1>CCCCCC.C(OCC)(=O)C>[CH3:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([N:18]2[CH2:19][CH2:20][N:21]([C:24]3[C:25]([CH3:38])=[C:26]([CH3:37])[C:27]4[O:31][C:30]([CH3:33])([CH3:32])[CH:29]([O:34][CH2:3][C:4]5[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=5)[C:28]=4[C:35]=3[CH3:36])[CH2:22][CH2:23]2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 23392Picolyl chloride hydrochlorideHCID 674202085-(4-(4-Methoxyphenyl)piperazin-1-yl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-ol

Product 1

HCID 184560411-(4-Methoxyphenyl)-4-(2,2,4,6,7-pentamethyl-3-(2-pyridylmethyl)oxy-2,3-dihydro-1-benzofuran-5-yl)piperazineYield 86%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Using 2-chloromethylpyridine hydrochloride and 5-(4-(4-methoxyphenyl)piperazin-1-yl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-ol obtained in Reference Example 18, the title compound was synthesized in the same manner as in Example 74. Yield 86%. mp. 120–121° C. (hexane-ethyl acetate). 1H-NMR (CDCl3) δ: 1.37 (3H, s), 1.59 (3H, s), 2.09 (3H, s), 2.25 (3H, s), 2.28 (3H, s), 3.05–3.28 (8H, m), 3.79 (3H, s), 4.67 (2H, s), 4.75 (1H, s), 6.86 (2H, d, J=9.2 Hz), 6.97 (2H, d, J=9.2 Hz), 7.15–7.21 (1H, m), 7.48 (1H, d, J=7.6 Hz), 7.68 (1H, t, J=7.6 Hz), 8.52 (1H, d, J=4.4 Hz).

Workup

  1. customobtained in Reference Example 18

Sources & evidence

ORD record
ord-f7fcd038dd254e1aa3b14d5c8ff62705
Source dataset
uspto-grants-2007_04
Patent number
US07208495B2

Reaction notes

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