Hydrazine → (Adamant-1-ylmethyl)hydrazine hydrochloride

HRID 1395183

Reaction equation

HRID 1395183 reaction equation
[NH2:1][NH2:2].[Cl:3][CH2:4][C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2.[OH-].[Na+]>CO.O>[ClH:3].[C:5]12([CH2:4][NH:1][NH2:2])[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2

Participants

6

Reactant 3

HCID 9321HydrazineHCID 14798Sodium HydroxideHCID 21039691-(Chloromethyl)adamantane

Product 1

HCID 20340449(Adamant-1-ylmethyl)hydrazine hydrochlorideYield 38.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4.0 g (120 mmol) of anhydrous hydrazine and 2.3 g (12 mmol) of 1-chloromethyladamantane were introduced into a sealable tube under nitrogen atmosphere. The tube was sealed and heated at 150° for 16 hours. After cooling to room temperature the contents were suspended in methanol, treated with a solution 0.5 g of sodium hydroxide in 1.5 ml of water, and the volatiles removed in vacuo. The resulting solid was extracted with ether and the solution dried with magnesium sulfate and treated with hydrogen chloride to give 1 g of the title compound (38% yield).

Workup

  1. customThe tube was sealed
  2. temperatureheated at 150° for 16 hours
  3. customthe volatiles removed in vacuo
  4. extractionThe resulting solid was extracted with ether
  5. dry with materialthe solution dried with magnesium sulfate
  6. additiontreated with hydrogen chloride

Sources & evidence

ORD record
ord-d19c0c7c64f745719d8f55933f50ae2d
Source dataset
uspto-grants-1980_05
Patent number
US04202892

Linked notes

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