2-Aminoadamantane hydrochloride → HCID 21454912, compound

HRID 436003Notes

Reaction equation

HRID 436003 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH2:11])[CH2:8]2.Cl.[CH:13]12[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH:14]1[NH2:23])[CH2:20]2.[C:24](N1C=CN=C1)(N1C=CN=C1)=[S:25]>O1CCCC1>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:24]([NH:23][CH:14]1[CH:15]3[CH2:21][CH:19]4[CH2:18][CH:17]([CH2:22][CH:13]1[CH2:20]4)[CH2:16]3)=[S:25])[CH2:8]2

Participants

5

Reactant 3

HCID 253312-Aminoadamantane hydrochlorideHCID 253322-AminoadamantaneHCID 802641,1'-Thiocarbonyldiimidazole

Product 1

HCID 21454912HCID 21454912, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 2-adamantylamine obtained from 5.0 g. (0.0266 mole) of 2-adamantylamine hydrochloride is reacted with 2.5 g. (0.014 mole) of 1,1'-thiocarbonyldiimidazole in 100 ml. of tetrahydrofuran for 20 hr. The solvent is evaporated and the residue partitioned between 5 percent hydrochloric acid and ether. The organic layer is washed with water, dried over potassium carbonate, evaporated and the residue is recrystallized from benzene-Skellysolve B: 3.65 g. (79 percent), m.p. 254-258.

Workup

  1. customThe solvent is evaporated
  2. customthe residue partitioned between 5 percent hydrochloric acid and ether
  3. washThe organic layer is washed with water
  4. dry with materialdried over potassium carbonate
  5. customevaporated
  6. customthe residue is recrystallized from benzene-Skellysolve B

Sources & evidence

ORD record
ord-8da82b64f5424a409d037ff6a50e9e64
Source dataset
uspto-grants-1977_02
Patent number
US04007181

Reaction notes

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