Morpholine → HCID 58213826, compound

HRID 1258950Notes

Reaction equation

HRID 1258950 reaction equation
[CH:1]([C:3]1[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=1[O:5][CH2:6][CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[CH:15]=2)[CH:10]=[CH:9]1)=O.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[O:28]1[CH2:29][CH2:30][N:25]([CH2:1][C:3]2[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=2[O:5][CH2:6][CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[CH:15]=3)[CH:10]=[CH:9]2)[CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 58213847HCID 58213847, compound

Product 1

HCID 58213826HCID 58213826, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of methyl 1-(2-(2-formylphenoxy)ethyl)-1H-indole-6-carboxylate (0.27 g, 0.84 mmol) and morpholine (0.22 mL, 2.5 mmol) in 1,2-dichloroethane (20 mL) was added NaBH(OAc)3 (0.35 g, 1.7 mmol). After stirring the solution for 4 hr at room temperature, the solution was concentrated and then diluted with ethyl acetate (100 mL) and washed with H2O (100 mL). The organic layer was dried (MgSO4), filtered and then concentrated to provide 0.33 g (˜100%) of methyl 1-(2-(2-(morpholinomethyl)phenoxy)ethyl)-1H-indole-6-carboxylate as an orange oil.

Workup

  1. concentrationthe solution was concentrated
  2. additiondiluted with ethyl acetate (100 mL)
  3. washwashed with H2O (100 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1ec75efc11074249b62045909a5671b0
Source dataset
uspto-grants-2013_06
Patent number
US08466193B2

Reaction notes

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