Formaldehyde → HCID 58514117, compound

HRID 1910736Notes

Reaction equation

HRID 1910736 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:11]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].Cl.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.[CH2:32]=O>O1CCOCC1>[N:26]1([CH2:32][CH2:2][C:1]([C:4]2[CH:5]=[C:6]([C:10]3[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17](=[O:24])[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:11]=3)[CH:7]=[CH:8][CH:9]=2)=[O:3])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 197884Morpholine, hydrochloride (1:1)HCID 58514094HCID 58514094, compound

Product 1

HCID 58514117HCID 58514117, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-[4-(3-Acetyl-phenyl)-pyridin-2-yl]-benzamide (200 mg, 0.632 mmol), morpholine HCl salt (78 mg, 0.632 mmol, 1 eq.) and paraformaldehyde (19 mg, 0.632 mmol, 1 eq.) were mixed with dioxane (2 mL) in a microwave tube. It was irradiated at 180° C. for 15 minutes. The mixture was partitioned between DCM/water (10 mL/5 mL). The aqueous layer was washed further with DCM (2×10 mL). The combined organic layer was dried (Na2SO4) and filtered. The filtrate was concentrated and the residue was chromatographed using 20/1 DCM/MeOH to give N-{4-[3-(3-Morpholin-4-yl-propionyl)-phenyl]-pyridin-2-yl}-benzamide as a slightly yellow solid (100 mg, 38%). MS: m/z 416.3 [MH+].

Workup

  1. customIt was irradiated at 180° C. for 15 minutes
  2. customThe mixture was partitioned between DCM/water (10 mL/5 mL)
  3. washThe aqueous layer was washed further with DCM (2×10 mL)
  4. dry with materialThe combined organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe residue was chromatographed

Sources & evidence

ORD record
ord-080acfc0b9ea495493a232b7d9e7f9aa
Source dataset
uspto-grants-2013_12
Patent number
US08604031B2

Reaction notes

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