N,N,N',N'-Tetramethylethylenediamine → HCID 67919426, compound

HRID 1493739Notes

Reaction equation

HRID 1493739 reaction equation
C([Li])CCC.[CH3:6][N:7]([CH3:20])[C:8]1[CH:9]=[C:10]([CH:17]=[CH:18][CH:19]=1)[CH2:11][C:12]1[NH:13][CH:14]=[CH:15][N:16]=1.CN(CCN(C)C)C.[CH:29]12[CH2:38][CH:33]3[CH2:34][CH:35]([CH2:37][CH:31]([CH2:32]3)[C:30]1=[O:39])[CH2:36]2>CCCCCC.C1COCC1.O>[CH3:20][N:7]([CH3:6])[C:8]1[CH:9]=[C:10]([CH:11]([C:30]2([OH:39])[CH:31]3[CH2:37][CH:35]4[CH2:34][CH:33]([CH2:38][CH:29]2[CH2:36]4)[CH2:32]3)[C:12]2[NH:16][CH:15]=[CH:14][N:13]=2)[CH:17]=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 64151AdamantanoneHCID 54307205HCID 54307205, compoundHCID 178418339Butyllithium

Product 1

HCID 67919426HCID 67919426, compoundYield 41.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

20 ml (31 mmol) of a 1.55 molar solution of n-butyllithium in hexane were added dropwise to a solution of 3.03 g (15 mmol) of (3-dimethylaminobenzyl)-imidazole and 1.75 g (15 mmol) of TMEDA in 30 ml of absolute THF. Stirring was carried out for 1 hour at -70° C., after which a solution of 2.26 g of adamantanone in 40 ml of absolute THF was added dropwise at -30° to -15° C. The mixture was allowed to warm up to room temperature in the course of about 45 minutes and was stirred for a further 2 hours at room temperature, 400 ml of water were added at 10° C., while cooling, and stirring was continued for 15 minutes at 0°-5° C., a crystalline precipitate being formed. This was filtered off under suction, rinsed with hexane and diisopropyl ether and dried in vacuo. 2.20 g (= 41.7% yield) of pure (3-dimethylaminophenyl)-(2-hydroxy-2-adamantyl)-1-imidazolylmethane of melting point 185° C. were obtained.

Workup

  1. stirringwas stirred for a further 2 hours at room temperature
  2. temperaturewhile cooling
  3. stirringstirring
  4. waitwas continued for 15 minutes at 0°-5° C.
  5. customa crystalline precipitate being formed
  6. filtrationThis was filtered off under suction
  7. washrinsed with hexane and diisopropyl ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-ff19ca17d666438bbb562088024d26ef
Source dataset
uspto-grants-1991_06
Patent number
US05023357

Reaction notes

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