Hydrochloric Acid → HCID 86612018, compound

HRID 1454181Notes

Reaction equation

HRID 1454181 reaction equation
C(CCCC(O)=O)(=O)C1C=CC=CC=1.CN(C)C1(C2C=CC=CC=2)CCC(N)CC1.CC(N=C=NC(C)C)C.ON1C2C=CC=CC=2N=N1.C(=O)([O-])[O-].[Na+].[Na+].Cl.[CH3:57][N:58]([CH3:85])[C:59]1([C:79]2[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=2)[CH2:64][CH2:63][CH:62]([NH:65][C:66](=[O:78])[CH2:67][CH2:68][CH2:69][C:70](=[O:77])[C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)[CH2:61][CH2:60]1.[Cl:86][Si](C)(C)C>CN(C=O)C.C(OC(=O)C)C.O>[ClH:86].[CH3:85][N:58]([CH3:57])[C:59]1([C:79]2[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=2)[CH2:64][CH2:63][CH:62]([NH:65][C:66](=[O:78])[CH2:67][CH2:68][CH2:69][C:70](=[O:77])[C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)[CH2:61][CH2:60]1

Participants

12

Reactant 8

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 10340Sodium CarbonateHCID 12734DiisopropylcarbodiimideHCID 73914delta-Oxobenzenepentanoic acidHCID 757711-HydroxybenzotriazoleHCID 11618103N-[4-(Dimethylamino)-4-phenylcyclohexyl]-δ-oxobenzenepentanamideHCID 129862564-Dimethylamino-4-phenyl-cyclohexylamine

Product 1

HCID 86612018HCID 86612018, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

280 mg 4-benzoylbutyric acid (5-oxo-5-phenyl pentanoic acid) dissolved in 1.4 ml DMF were added to 350 mg of the non-polar diastereoisomer of N,N-dimethyl-1-phenylcyclohexane-1,4-diamine, 230 μl N,N-diisopropylcarbodiimide and 200 μg 1-hydroxybenzotriazole (HOBt) at about 5° C. while stirring. After three hours at this temperature, the mixture was stirred overnight while heating to room temperature. For working up, one-molar sodium carbonate solution was added (pH>10) and the crude product (674 mg) isolated by extraction with ethylacetate, subsequent drying over sodium sulphate and evaporation. The main fraction of 295 mg obtained by column chromatography on silica gel (4.0×18 cm) with methanol/ethylacetate/n-hexane (V:V:V=1:1:1) was dissolved in 135 ml ethylacetate and was converted into the corresponding hydrochloride of the non-polar diastereoisomer of 5-oxo-5-phenyl pentanoic acid (4-dimethylamino-4-phenylcyclohexyl)amide by adding 12 μl water and 90 μl chlorotrimethylsilane (310 mg white solid, mp. 127-137° C.).

Workup

  1. stirringthe mixture was stirred overnight
  2. dry with materialsubsequent drying over sodium sulphate and evaporation
  3. customThe main fraction of 295 mg obtained by column chromatography on silica gel (4.0×18 cm) with methanol/ethylacetate/n-hexane (V:V:V=1:1:1)

Sources & evidence

ORD record
ord-315e4063a1004bf1ab4c785b63e6807b
Source dataset
uspto-grants-2009_01
Patent number
US07476763B2

Reaction notes

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