Pyridine → HCID 59536567, compound

HRID 1963236Notes

Reaction equation

HRID 1963236 reaction equation
[C:1]([CH:4]1[CH2:9][CH:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:7][CH2:6][N:5]1[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])(=O)[NH2:2].N1C=CC=CC=1.O=S(Cl)Cl>>[C:1]([CH:4]1[CH2:9][CH:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:7][CH2:6][N:5]1[C:15]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16])#[N:2]

Participants

4

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 59536565HCID 59536565, compound

Product 1

HCID 59536567HCID 59536567, compoundYield 99.1%

Procedure

1-Benzyl 4-ethyl 2-carbamoylpiperidine-1,4-dicarboxylate (2.4 g, 7.18 mmol) was dissolved in pyridine (50 mL, 618.21 mmol). The mixture was cooled on an ice bath and SOCl2 (3.14 mL, 43.07 mmol) was added dropwise and left overnight at room temperature. The reaction mixture was evaporated and partitioned between diluted HCl and DCM. The aqueous layer was extracted with DCM and the combined organic layer was washed with water, dried over Na2SO4 and evaporated. Crude 1-benzyl 4-ethyl 2-cyanopiperidine-1,4-dicarboxylate (2.25 g, 99%) was isolated. 1H NMR (400 MHz, dmso) δ 1.21 (t, 3H), 1.54-1.66 (m, 1H), 1.98-2.12 (m, 2H), 2.29-2.37 (m, 1H), 2.83-2.91 (m, 1H), 3.04-3.16 (m, 1H), 3.83-3.91 (m, 1H), 4.02-4.18 (m, 2H), 5.13 (s, 2H), 5.25-5.31 (m, 1H), 7.28-7.40 (m, 5H).

Workup

  1. temperatureThe mixture was cooled on an ice bath
  2. customThe reaction mixture was evaporated
  3. custompartitioned between diluted HCl and DCM
  4. extractionThe aqueous layer was extracted with DCM
  5. washthe combined organic layer was washed with water
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-012009d810c042c3848290f14a842ab4
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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