Cyclopropylamine → HCID 43403632, compound

HRID 1158428Notes

Reaction equation

HRID 1158428 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7]OS(C1C=CC(C)=CC=1)(=O)=O.[CH:19]1([NH2:22])[CH2:21][CH2:20]1>>[CH:19]1([NH:22][CH2:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)[CH2:21][CH2:20]1

Participants

3

Reactant 2

HCID 69828CyclopropylamineHCID 12641003HCID 12641003, compound

Product 1

HCID 43403632HCID 43403632, compound

Conditions

Temperature
110 °C

Procedure

A mixture of toluene-4-sulfonic acid tetrahydro-pyran-2-ylmethyl ester (500 mg, 1.85 mmol) and cyclopropylamine (2 mL, 15 mmol) is heated overnight at 110° C. in a sealed tube. The crude mixture is concentrated and taken up in CH2Cl2. Water is added, the layers are separated and the aqueous one back extracted twice with CH2Cl2. The combined organic extracts are washed with brine, dried over Na2SO4, filtered and concentrated. TLC, Rf (CH2Cl2/MeOH 95:5)=0.3, MS (LC-MS): 156.2 [M+H]+.

Workup

  1. concentrationThe crude mixture is concentrated
  2. additionWater is added
  3. customthe layers are separated
  4. extractionthe aqueous one back extracted twice with CH2Cl2
  5. washThe combined organic extracts are washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-495aaec245784a8d89965adb21d256c8
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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