Tert-Butylamine → HCID 58124834, compound

HRID 1971750Notes

Reaction equation

HRID 1971750 reaction equation
CS(O[CH2:6][CH2:7][C:8]([CH3:13])([CH3:12])[CH2:9][C:10]#[CH:11])(=O)=O.[C:14]([NH2:18])([CH3:17])([CH3:16])[CH3:15]>>[C:14]([NH:18][CH2:6][CH2:7][C:8]([CH3:13])([CH3:12])[CH2:9][C:10]#[CH:11])([CH3:17])([CH3:16])[CH3:15]

Participants

3

Reactant 2

HCID 6385Tert-ButylamineHCID 59378464HCID 59378464, compound

Product 1

HCID 58124834HCID 58124834, compound

Procedure

A solution of 1.3 g of 24b in 15 ml of tert.butylamine, was heated in a closed vessel at an oil bath at 70° C. for 4 days. The reaction was concentrated (rotavap, 150 mB, 40° C.) and then diluted with water and acidified with 1N HCl. The organic layer was washed twice with ether. The aqueous phase was made alkaline (2N NaOH) and extracted with diethylether. The organic material was dried and concentrated (100 mm, 40° C.) to give 960 mg of amine 24c, as a colorless oil. NMR (CDCl3) δ 1.00 (s, 6, 2×CH3), 1.11 (s, 9, tertC4H9), 1.47 (m, 2, CH2), 1.98 (t, 1, acetylene), 2.10 (d, 2, CH2), 2.55 (m, 2, CH2).

Workup

  1. concentrationThe reaction was concentrated (rotavap, 150 mB, 40° C.)
  2. additiondiluted with water
  3. washThe organic layer was washed twice with ether
  4. extractionextracted with diethylether
  5. customThe organic material was dried
  6. concentrationconcentrated (100 mm, 40° C.)

Sources & evidence

ORD record
ord-7627d2ea4c0d4005bd7a7593de350d80
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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