Sodium Carbonate → 1-Phenyl-1-cyclohexyl-3-(2-tritylaminoethyl)amino-1-propanol

HRID 1074159Notes

Reaction equation

HRID 1074159 reaction equation
[C:1]([NH:20][CH2:21][CH2:22][NH2:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:30]1([C:36]([CH:41]2[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]2)([OH:40])[CH2:37][CH2:38]Cl)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(O)CCC.O>[C:30]1([C:36]([CH:41]2[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]2)([OH:40])[CH2:37][CH2:38][NH:23][CH2:22][CH2:21][NH:20][C:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2794294N-tritylethylenediamineHCID 138411961-Phenyl-1-cyclohexyl-3-chloro-1-propanol

Product 1

HCID 221558931-Phenyl-1-cyclohexyl-3-(2-tritylaminoethyl)amino-1-propanolYield 61.7%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolvent2×HCID 962WaterSolvent

Procedure

To a mixture of N-tritylethylenediamin (3.66 g) and sodium carbonate (9.2 g) in n-butanol (20 ml), a solution of 1-phenyl-1-cyclohexyl-3-chloro-1-propanol (3 g) in butanol (10 ml) was added. The mixture was refluxed overnight, then cooled, diluted with water and extracted with ethyl acetate. The solvent was dried and evaporated. The residue was purified by column chromatography (methylene chloride, methanol, ammonia 99:1:0.1) to afford 3.8 g of 1-phenyl-1-cyclohexyl-3-(2-tritylaminoethyl)amino-1-propanol. M.p. 198° C.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. temperaturecooled
  3. extractionextracted with ethyl acetate
  4. customThe solvent was dried
  5. customevaporated
  6. customThe residue was purified by column chromatography (methylene chloride, methanol, ammonia 99:1:0.1)

Sources & evidence

ORD record
ord-f16a00da4a854242a00f90236b9c3b57
Source dataset
uspto-grants-1990_11
Patent number
US04973592

Reaction notes

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