Formaldehyde → HCID 68770660, compound

HRID 1947449Notes

Reaction equation

HRID 1947449 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:10][C:11](=[O:13])[CH3:12])[CH:8]=2)[CH:3]=[CH:2]1.[CH2:14]=O.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>O1CCOCC1.C(O)(=O)C>[N:16]1([CH2:14][C:3]2[C:4]3[C:9](=[CH:8][C:7]([O:10][C:11](=[O:13])[CH3:12])=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8083MorpholineHCID 14529092HCID 14529092, compound

Product 1

HCID 68770660HCID 68770660, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 22565020HOAc dioxaneSolvent

Procedure

To a solution of acetic acid 1H-indol-6-yl ester (2.0 g, 11.4 mmol) in dioxane/acetic acid (1:1, 114 mL) was added formaldehyde (0.85 mL, 0.93 g, 11.4 mmol) and morpholine (1 mL, 1 g, 11.4 mmol) and the resulting mixture was stirred (rt, 16 h). The reaction mixture was concentrated in vacuo, diluted with DCM (200 mL) and washed with 1N NaOH (20 mL), 4 N NaOH (20 mL) and brine (2×10 mL). The organic layer was dried, filtered and concentrated in vacuo to provide the title compound (2.87 g, 92%). MS (ESI): mass calculated for C15H18N2O3, 274.1; m/z found, 275.1 [M+H]+. 1H NMR (600 MHz, CDCl3): 8.09 (s, 1H), 7.73 (d, J=8.5, 1H), 7.11 (dd, J=11.7, 2.1, 2H), 6.85 (dd, J=8.5, 2.0, 1H), 3.71-3.68 (m, 4H), 3.67 (s, 2H), 2.48 (s, 4H), 2.32 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with DCM (200 mL)
  3. washwashed with 1N NaOH (20 mL), 4 N NaOH (20 mL) and brine (2×10 mL)
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e20ba4c313e44bab3785f3313b80078
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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