2-Aminoadamantane hydrochloride → HCID 59830701, compound

HRID 2424911Notes

Reaction equation

HRID 2424911 reaction equation
C(Cl)(=O)C(Cl)=O.[CH2:7]([C:11]1[N:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=O)[CH2:8][CH2:9][CH3:10].Cl.[CH:22]12[CH2:31][CH:26]3[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]3)[CH:23]1[NH2:32])[CH2:29]2.C(N(C(C)C)C(C)C)C>ClCCl>[CH:22]12[CH2:31][CH:26]3[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]3)[CH:23]1[NH:32][C:13](=[O:15])[C:12]1[CH:16]=[CH:17][C:18]([Cl:20])=[N:19][C:11]=1[CH2:7][CH2:8][CH2:9][CH3:10])[CH2:29]2

Participants

6

Reactant 4

HCID 253312-Aminoadamantane hydrochlorideHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 59830749HCID 59830749, compound

Product 1

HCID 59830701HCID 59830701, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

A solution of oxalyl chloride (0.105 mL, 1.20 mmol) in dichloromethane (2 mL) was added dropwise to a stirred suspension of 2-butyl-6-chloronicotinic acid (214 mg, 1.00 mmol), in dichloromethane (25 mL) over a period of 2 minutes under nitrogen. The resulting solution was stirred at room temperature for 4 hours. The reaction mixture was evaporated to dryness and dissolved in DCM (5 mL). This solution was added dropwise to a stirred solution of 2-adamantanamine hydrochloride (188 mg, 1.00 mmol) and N-ethyldiisopropylamine (0.693 mL, 4.01 mmol) in dichloromethane (20 mL) over a period of 2 minutes under nitrogen. The resulting solution was stirred at room temperature for 16 hours. The reaction mixture was diluted with DCM (20 mL), and washed sequentially with 0.1M HCl (20 mL), saturated NaHCO3 (20 mL), and saturated brine (20 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford N-adamantan-2-yl-2-butyl-6-chloronicotinamide (290 mg, 83%)

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutiondissolved in DCM (5 mL)
  3. stirringThe resulting solution was stirred at room temperature for 16 hours
  4. washwashed sequentially with 0.1M HCl (20 mL), saturated NaHCO3 (20 mL), and saturated brine (20 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-213b7d168cdd4b0d8529c83879abc368
Source dataset
uspto-grants-2011_06
Patent number
US07964618B2

Reaction notes

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