Tert-Butylamine → N-tert-butyl-3-(prop-2-ynyloxy)propan-1-amine

HRID 1971656Notes

Reaction equation

HRID 1971656 reaction equation
CS(O)(=O)=O.CS(O[CH2:11][CH2:12][CH2:13][O:14][CH2:15][C:16]#[CH:17])(=O)=O.[C:18]([NH2:22])([CH3:21])([CH3:20])[CH3:19]>>[C:18]([NH:22][CH2:11][CH2:12][CH2:13][O:14][CH2:15][C:16]#[CH:17])([CH3:21])([CH3:20])[CH3:19]

Participants

4

Reactant 3

HCID 6385Tert-ButylamineHCID 6395Methanesulfonic AcidHCID 872051893-(Prop-2-ynyloxy)propyl methanesulfonate

Product 1

HCID 58124800N-tert-butyl-3-(prop-2-ynyloxy)propan-1-amine

Procedure

A solution of 1 g of methane sulphonic acid and 1 g of 7d in 10 ml of tert-C4H9NH2 was heated at 60° C. for 24 hr in a closed vial. The reaction mixture was concentrated and the residue was diluted with 15 ml of 1M aq. K2CO3. Then, the product was extracted with ethyl acetate. The organic layer was washed once with sat. NaCl solution, dried and concentrated to provide 830 mg of 7e as a yellowish oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was diluted with 15 ml of 1M aq. K2CO3
  3. extractionThen, the product was extracted with ethyl acetate
  4. washThe organic layer was washed once with sat. NaCl solution
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dd35780540a94e6dad14b560d5e7b0d2
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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