Dichloromethane → (4-fluorotetrahydro-2H-pyran-4-yl)methanamine

HRID 2273784Notes

Reaction equation

HRID 2273784 reaction equation
[F:1][C:2]1([CH2:8][N:9]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.NN.C(Cl)Cl>C(O)C>[F:1][C:2]1([CH2:8][NH2:9])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 9321HydrazineHCID 671270062-((4-Fluorotetrahydro-2h-pyran-4-yl)methyl)isoindoline-1,3-dione

Product 1

HCID 46856407(4-fluorotetrahydro-2H-pyran-4-yl)methanamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of EXAMPLE 409B (1.4 g) and hydrazine (1.548 mL) in ethanol (40 mL) was heated at 70° C. overnight, cooled to room temperature, slurried with CH2Cl2 (200 mL) and the solid removed by filtration. The filtrate was concentrated and chromatographed on silica gel with 100:5:1 ethyl acetate/methanol/NH4OH as eluent to give the product.

Workup

  1. customthe solid removed by filtration
  2. concentrationThe filtrate was concentrated
  3. customchromatographed on silica gel with 100:5:1 ethyl acetate/methanol/NH4OH as eluent
  4. customto give the product

Sources & evidence

ORD record
ord-7dbcd8dffc8d45799c87381d0217a1f0
Source dataset
uspto-grants-2015_09
Patent number
US09125913B2

Reaction notes

Loading…