Hydrazine hydrate (1:1) → HCID 86705518, compound

HRID 2279519Notes

Reaction equation

HRID 2279519 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]([C@H:21]2[CH2:25][CH2:24][CH2:23][N:22]2[CH3:26])[N:10]2C(=O)C3C(=CC=CC=3)C2=O)[CH:5]=[CH:6][C:7]=1[Cl:8].CO.C1COCC1.O.NN>O>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]([C@H:21]2[CH2:25][CH2:24][CH2:23][N:22]2[CH3:26])[NH2:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 21899815MeOH tetrahydrofuranHCID 86705517HCID 86705517, compound

Product 1

HCID 86705518HCID 86705518, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 244 (0.40 g, 1.03 mmol) and MeOH:THF (1:1, 10 mL) was added hydrazine monohydrate (0.514 g, 10.3 mmol) and the reaction was stirred at 50° C. for 18 h. The reaction mixture was poured into water and extracted with DCM. The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (500:50) to afford 0.130 g (48.8%) of (S)-(3,4-dichlorophenyl)((R)-1-methylpyrrolidin-2-yl)methanamine (246).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by SiO2 chromatography
  6. washeluting with DCM/MeOH (500:50)

Sources & evidence

ORD record
ord-117e67dc973f436ab9d2d542139f01f0
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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