Cyclopropanemethanamine → HCID 63376557, compound

HRID 2274458Notes

Reaction equation

HRID 2274458 reaction equation
[CH:1]1([CH2:4][NH2:5])[CH2:3][CH2:2]1.Cl[C:7]1[N:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10]>C(O)(C)(C)C.ClCCl>[Cl:16][C:14]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[C:7]([NH:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)[N:15]=1

Participants

5

Reactant 2

HCID 75646CyclopropanemethanamineHCID 8540472,6-Dichloronicotinic acid

Product 1

HCID 63376557HCID 63376557, compoundYield 107.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
170 °C

Procedure

In a sealable tube, 3 g (42 mmol) of cyclopropylmethylamine is added to 3 g (14 mmol) of 2,6-dichloronicotinic acid in solution in tert-butanol (14 ml), the tube is sealed and heated at 170° C. for 30 minutes in a Biotage Initiator microwave. The reaction mixture is cooled to room temperature, diluted in dichloromethane (100 ml) and washed with a 10% aqueous solution of acetic acid (12 ml). The organic phase is dried over Na2SO4, filtered, concentrated and dried under vacuum. 3.4 g of product is obtained in the form of an orange oil.

Workup

  1. customthe tube is sealed
  2. temperatureThe reaction mixture is cooled to room temperature
  3. washwashed with a 10% aqueous solution of acetic acid (12 ml)
  4. dry with materialThe organic phase is dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried under vacuum

Sources & evidence

ORD record
ord-3f69ababea4447e1be99199a02e5261c
Source dataset
uspto-grants-2015_09
Patent number
US09126972B2

Reaction notes

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