Trityl chloride → HCID 18919397, compound

HRID 1291011Notes

Reaction equation

HRID 1291011 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([NH2:8])[CH2:4][CH2:3]1.C(N(CC)CC)C.[C:16]1([C:22](Cl)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl>[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 183741,4-Diaminocyclohexane

Product 1

HCID 18919397HCID 18919397, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1,4-Diaminocyclohexane (cis, trans mixture) (24.0 g, 210 mmol) and triethylamine (16.3 ml, 117 mmol) were dissolved in methylene chloride (400 ml). A solution of triphenylmethyl chloride (32.5 g, 117 mmol) dissolved in methylene chloride (100 ml) was dropwise added under ice-cooling and the mixture was stirred for 15 minutes and at room temperature for 45 minutes. The reaction mixture was filtrated and low boiling matters were distilled away from the filtrate under reduced pressure. Water (100 ml) was added to the residue and extracted with chloroform. The extract was dried over anhydrous sodium sulfate. After filtration, low boiling matters were distilled away from the filtrate under reduced pressure. The residue was purified by silica gel (Chromatorex, NH type, Fuji Silysia Chemical) column chromatography (chloroform/n-hexane=5/1-10/1) to give 18.4 g of 1-amino-4-(triphenylmethylamino)cyclohexane as a pale-yellow oil (25%).

Workup

  1. additionwas dropwise added under ice-
  2. temperaturecooling
  3. filtrationThe reaction mixture was filtrated
  4. distillationlow boiling matters were distilled away from the filtrate under reduced pressure
  5. additionWater (100 ml) was added to the residue
  6. extractionextracted with chloroform
  7. dry with materialThe extract was dried over anhydrous sodium sulfate
  8. filtrationAfter filtration, low boiling matters
  9. distillationwere distilled away from the filtrate under reduced pressure
  10. customThe residue was purified by silica gel (Chromatorex, NH type, Fuji Silysia Chemical) column chromatography (chloroform/n-hexane=5/1-10/1)

Sources & evidence

ORD record
ord-cde2def8549a4e3c87df9c76ae3ec760
Source dataset
uspto-grants-1998_05
Patent number
US05753670

Reaction notes

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