1-C-Ethylaminoadamantane → HCID 18782790, compound

HRID 1420788

Reaction equation

HRID 1420788 reaction equation
[C:1]12([CH2:11][CH2:12][NH2:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:14](N1C=CN=C1)(N1C=CN=C1)=[S:15]>C(Cl)Cl.N#N>[N:13]([CH2:12][CH2:11][C:1]12[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2)=[C:14]=[S:15]

Participants

5

Reactant 2

HCID 642451-C-EthylaminoadamantaneHCID 802641,1'-Thiocarbonyldiimidazole

Product 1

HCID 18782790HCID 18782790, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 947NitrogenSolventHCID 6344DichloromethaneSolvent

Procedure

2-adamantan-1-yl-ethylamine (380 mg, 2.12 mmol) was dissolved in CH2Cl2 (10 ml) under a dry atmosphere of N2. To this solution was added 1,1'-thiocarbonyl-diimidazole (420 mg, 2.12 mmol). After stirring at ambient temperature for 12 hours, the solution was partitioned between 0.1 N HCl and CH2Cl2. The CH2Cl2 layer was washed with water, then saturated NaHCO3 solution and finally brine. The CH2Cl2 layer was dried over MgSO4, filtered and concentrated under vacuum to give 417 mg of a yellow solid. The product was chromatographed on silica gel using hexanes to give 125 mg of the titled compound as a white solid: 1H NMR (CDCl3)δ 3.52 (m, 2H), 1.98 (br s, 3H), 1.49-1.76 (m, 17H).

Workup

  1. customthe solution was partitioned between 0.1 N HCl and CH2Cl2
  2. washThe CH2Cl2 layer was washed with water
  3. dry with materialThe CH2Cl2 layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-553a9219c3b547e9887188910e82814f
Source dataset
uspto-grants-2000_06
Patent number
US06071935

Linked notes

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