Ethanol → N1-Adamantan-2-yl-2-methyl-propane-1,2-diamine

HRID 1092332Notes

Reaction equation

HRID 1092332 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[C:2]1=O)[CH2:8]2.[NH2:12][CH2:13][CH:14]([NH2:16])[CH3:15].[BH4-].[Na+].[CH2:19](O)C>>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:12][CH2:13][C:14]([CH3:19])([NH2:16])[CH3:15])[CH2:8]2

Participants

5

Reactant 4

HCID 702EthanolHCID 6567PropylenediamineHCID 64151AdamantanoneHCID 4311764Sodium borohydride

Product 1

HCID 84088000N1-Adamantan-2-yl-2-methyl-propane-1,2-diamine

Conditions

Temperature
0 °C

Procedure

In analogy to a procedure outlined in J. Med. Chem. 32, 1989, 179-182, 2-adamantanone (500 mg) and 1,2-diaminopropane (440 mg) were dissolved in dry ethanol (12 mL) and heated to reflux for 1.5 hours. The mixture was cooled to 0° C. and sodium borohydride (164 mg) was added in portions over 5 minutes). The mixture was allowed to stir at RT for 12 hours. The mixture was evaporated and the residue was dissolved in CHCl3, washed with saturated NaHCO3 solution and brine, dried over Na2SO4 and evaporated. The residue was dried in vacuo to give a slightly yellow liquid that was used without further purification. MS (ESI): 223.4 (MH+).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1.5 hours
  3. customThe mixture was evaporated
  4. dissolutionthe residue was dissolved in CHCl3
  5. washwashed with saturated NaHCO3 solution and brine
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe residue was dried in vacuo
  9. customto give a slightly yellow liquid that
  10. customwas used without further purification

Sources & evidence

ORD record
ord-a67037438d324cd989d81bae4ee30d8e
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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