Piperidine → 2-[3-Methoxy-4-(piperidin-1-ylmethyl)phenyl]-1,3-benzoxazole

HRID 7749Notes

Reaction equation

HRID 7749 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[O:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH:6]=[CH:7][C:8]=1[CH2:9][N:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1.Br[CH2:25]C1C=CC(C2OC3C=CC=CC=3N=2)=CC=1OC.N1CCCCC1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[O:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH:6]=[CH:7][C:8]=1[CH2:9][N:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:25]1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 102365762-[3-Methoxy-4-(pyrrolidin-1-ylmethyl)phenyl]-1,3-benzoxazoleHCID 219909912-[4-(Bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole

Product 1

HCID 102865172-[3-Methoxy-4-(piperidin-1-ylmethyl)phenyl]-1,3-benzoxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Utilizing the general procedure outlined for 2-[3-methoxy-4-(pyrrolidin-1-ylmethyl)phenyl]-1,3-benzoxazole, 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (300 mg, 0.942 mmol) was reacted with piperidine (279 μL, 2.83 mmol) and triethylamine (394 μL, 2.83 mmol) in CH2Cl2 (5 mL) to afford the desired 2-[3-methoxy-4-(piperidin-1-ylmethyl)phenyl]-1,3-benzoxazole as a colorless solid: 1H NMR (CDCl3-d, 300 MHz) δ 7.86–7.83 (m, 1H), 7.79–7.76 (m, 1H), 7.73 (s, 1H), 7.61–7.55 (m, 2H), 7.37–7.34 (m, 2H), 3.96 (s, 3H), 3.59 (s, 2H), 2.47 (br, 4H), 1.66–1.58 (m, 4H), 1.46–1.45 (m, 2H). MS (ESI) 323 (M+)+.

Sources & evidence

ORD record
ord-c59404332d6248c9b8b4adb3a1b959e4
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Reaction notes

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