Dimethylformamide → 5-[(morpholin-4-yl)methyl]-1H-pyrrole-2-carbaldehyde

HRID 44251Notes

Reaction equation

CN([CH:4]=[O:5])C.O=P(Cl)(Cl)Cl.[NH:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.C([O-])(=O)C.[K+].[OH-].[Na+]>C(Cl)Cl>[N:17]1([CH2:16][C:12]2[NH:11][C:15]([CH:4]=[O:5])=[CH:14][CH:13]=2)[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of DMF (18.04 mmoles) in DCM (10 ml) there is added POCl3, dropwise, at 0° C. After stirring for 5 minutes, a solution of the compound obtained in Step A (9.02 mmoles) is added dropwise. After stirring for 3 hours at 0° C., the reaction mixture is heated at 40° C. for 30 minutes. At ambient temperature, an aqueous solution of potassium acetate (32 mmoles) is added and then the reaction mixture is stirred at 40° C. for 30 minutes. At ambient temperature, the solution is brought to alkaline pH using 2M NaOH solution and is then extracted with DCM. The organic phase is washed with water and with saturated NaCl solution, dried over sodium sulphate, filtered and evaporated to dryness. The residue obtained is purified on silica gel (SiO2; gradient DCM/AcOEt) to yield the title product.

Workup

customat 0° C
stirringAfter stirring for 3 hours at 0° C.
stirringthe reaction mixture is stirred at 40° C. for 30 minutes
customAt ambient temperature
extractionis then extracted with DCM
washThe organic phase is washed with water and with saturated NaCl solution
dry with materialdried over sodium sulphate
filtrationfiltered
customevaporated to dryness
customThe residue obtained
customis purified on silica gel (SiO2; gradient DCM/AcOEt)

Sources & evidence

ORD record: ord-60a072c7bae94c2991b33f404f72a107
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541412B2

Reaction notes

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