Cyclamate → HCID 53757270, compound

HRID 917896Notes

Reaction equation

HRID 917896 reaction equation
OC1C=CC(N2C3C(=CC=CC=3)C=C2C2C=CC=CC=2)=CC=1.C[O-].[Na+].ClCCN1CCCC1.C1(NS(O)(=O)=O)CCCCC1.C1(NS(O)(=O)=O)CCCCC1.[N:56]1([CH2:61][CH2:62][O:63][C:64]2[CH:69]=[CH:68][C:67]([N:70]3[C:78]4[C:73](=[CH:74][CH:75]=[CH:76][CH:77]=4)[CH:72]=[C:71]3[C:79]3[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=3)=[CH:66][CH:65]=2)[CH2:60][CH2:59][CH2:58][CH2:57]1>CC(C)=O.C(O)(C)C.CCOCC.ClC1C=CC=CC=1.CO>[N:56]1([CH2:61][CH2:62][O:63][C:64]2[CH:65]=[CH:66][C:67]([N:70]3[C:78]4[C:73](=[CH:74][CH:75]=[CH:76][CH:77]=4)[CH:72]=[C:71]3[C:79]3[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=3)=[CH:68][CH:69]=2)[CH2:57][CH2:58][CH2:59][CH2:60]1

Participants

11

Reactant 5

HCID 7533CyclamateHCID 816691-(2-Chloroethyl)pyrrolidineHCID 10942334Sodium MethoxideHCID 21523973HCID 21523973, compoundHCID 131710383HCID 131710383, compound

Product 1

HCID 53757270HCID 53757270, compound

Reagents, catalysts & solvents 5

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolventHCID 7964ChlorobenzeneSolvent2×

Procedure

Following a procedure similar to that of Example 1E but using 28.53 g. of 1-(4-hydroxyphenyl)-2-phenylindole, 300 ml. of chlorobenzene, 5.5 g. of sodium methoxide in 50 ml. of dry methyl alcohol, and N-(2-chloroethyl)pyrrolidine in 100 ml. of chlorobenzene there was obtained 36 g. of crude product, a solution of 35 g. of which was dissolved in hot acetone, treated with a solution of 18 g. of cyclohexanesulfamic acid, diluted with 200 ml. of ether to give, on recrystallization from isopropyl alcohol, 25.8 g. of 1 -{4-[2-(1-pyrrolidyl)ethoxy]-phenyl}-2-phenylindole cyclohexane sulfamate; m.p. 152.5°-153.5°C.

Workup

  1. additiontreated with a solution of 18 g

Sources & evidence

ORD record
ord-4e7a2bd184584ea78c58d6877da7c429
Source dataset
uspto-grants-1976_07
Patent number
US03968121

Reaction notes

Loading…