Water → HCID 12071670, compound

HRID 413265Notes

Reaction equation

HRID 413265 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[C:20]1([O:26][C:27](Cl)=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>C(Cl)Cl>[C:20]1([O:26][C:27](=[O:28])[NH:13][C:10]2[CH:11]=[CH:12][C:7]([N:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[N:8][CH:9]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 15891Phenyl chloroformateHCID 102413536-(1-PIPERIDINYL)-3-PYRIDINAMINE

Product 1

HCID 12071670HCID 12071670, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,4,5,6-Tetrahydro-2H-[1,2′]bipyridinyl-5′-ylamine (1.01 g, 5.7 mmol) and pyridine (12 ml) are stirred in dry CH2Cl2. Phenylchloroformate (1.3 g, 8.5 mmol) is added to this mixture and stirred for 24 h at room temperature. Water and a solution of 1:1 EtOAc/hexanes is added and the organic layer is separated. The organic layer is washed with 1N HCl three times and with brine once. The organic layer is dried over Na2SO4, filter, and evaporated in vacuo. Purify by flash column chromatography (0-10% EtOAc/CH2Cl2) to obtain (3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-yl)-carbamic acid phenyl ester. Mass spec.: M−1=280 (AP−).

Workup

  1. customthe organic layer is separated
  2. washThe organic layer is washed with 1N HCl three times and with brine once
  3. dry with materialThe organic layer is dried over Na2SO4
  4. filtrationfilter
  5. customevaporated in vacuo
  6. customPurify by flash column chromatography (0-10% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-b92d8c6ac1df444c8f1294578a8e8086
Source dataset
uspto-grants-2003_05
Patent number
US06566367B2

Reaction notes

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