1-C-Ethylaminoadamantane → HCID 18381547, compound

HRID 2298076Notes

Reaction equation

HRID 2298076 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C([N:19]1[CH:23]=[CH:22]N=C1)(N1C=CN=C1)=O.[C:24]12(CCN)[CH2:33][CH:28]3[CH2:29]C([CH2:32][CH:26]([CH2:27]3)[CH2:25]1)[CH2:31]2>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:19][CH2:23][C:22]12[CH2:32][CH:26]3[CH2:27][CH:28]([CH2:33][CH:24]([CH2:25]3)[CH2:31]1)[CH2:29]2)=[O:6]

Participants

5

Reactant 3

HCID 642451-C-EthylaminoadamantaneHCID 682631,1'-CarbonyldiimidazoleHCID 918212-Chloro-4-hydroxybenzoic acid

Product 1

HCID 18381547HCID 18381547, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-4-hydroxybenzoic acid (3.30 g) in dimethylformamide (20 ml) was added 1,1′-carbonyldiimidazole (3.30 g). The reaction mixture was stirred for 2.5 h and then 1-adamantanethylamine (3.4 ml) was added. After 14 h the reaction mixture was partitioned between ethyl acetate and 2N aqueous hydrochloric acid and the organic layer was separated, washed with water then brine and dried (MgSO4). The organic layer was concentrated under reduced pressure to give a residue which was purified by silica gel chromatography (eluting with 10-70% ethyl acetate in dichloromethane) to yield a white solid which was triturated with ethyl acetate to yield the subtitle compound as a white solid (3.6 g).

Workup

  1. customAfter 14 h the reaction mixture was partitioned between ethyl acetate and 2N aqueous hydrochloric acid
  2. customthe organic layer was separated
  3. washwashed with water
  4. dry with materialbrine and dried (MgSO4)
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customto give a residue which
  7. customwas purified by silica gel chromatography (eluting with 10-70% ethyl acetate in dichloromethane)
  8. customto yield a white solid which
  9. customwas triturated with ethyl acetate

Sources & evidence

ORD record
ord-5734fea0d0824151b68178461b679e5a
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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