Morpholine → 2-[3-Chloro-4-(2-morpholin-4-ylethyl)phenyl]-1,3-benzoxazole

HRID 7753Notes

Reaction equation

HRID 7753 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH:17]=O)=[C:12]([Cl:19])[CH:11]=1.[BH3-]C#N.[Na+].[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>CO.C(Cl)Cl>[Cl:19][C:12]1[CH:11]=[C:10]([C:2]2[O:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)[CH:15]=[CH:14][C:13]=1[CH2:16][CH2:17][N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 5003444Sodium cyanoborohydrideHCID 87899469HCID 87899469, compound

Product 1

HCID 101259462-[3-Chloro-4-(2-morpholin-4-ylethyl)phenyl]-1,3-benzoxazole

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The crude aldehyde was treated with NaCNBH3 and morpholine in MeOH/CH2Cl2 (2 mL). The crude mixture was adsorbed onto silica gel and purified by automated flash chromatography using an EtOAc/hexanes gradient to afford the desired 2-[3-chloro-4-(2-morpholin-4-ylethyl)phenyl]-1,3-benzoxazole: 1H NMR (CDCl3, 300 MHz) δ 8.26–8.25 (d, 1H), 8.09–8.06 (m, 1H), 7.79–7.74 (m, 1H), 7.43–7.34 (m, 3H), 3.78–3.75 (m, 4H), 3.05–3.00 (m, 2H), 2.68–2.59 (m, 6H). MS (ESI) 343 (M+H)+.

Workup

  1. custompurified by automated flash chromatography

Sources & evidence

ORD record
ord-8cb6b06cc4ed41c8af5693e089fd16b2
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Reaction notes

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