Ammonia → HCID 12803181, compound

HRID 1381548Notes

Reaction equation

HRID 1381548 reaction equation
[C:1]([CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][C:14]([NH2:16])=[O:15])[CH:11]=2)[NH:6][CH:5]=1)#[N:2].N>[Ni].CCO>[NH2:2][CH2:1][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][C:14]([NH2:16])=[O:15])[CH:11]=2)[NH:6][CH:5]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 12803105HCID 12803105, compound

Product 1

HCID 12803181HCID 12803181, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

A suspension of 11.0 g (0.05 mole) of N-(3-cyanomethyl-1H-indol-5-yl)urea in 700 ml of abs. EtOH saturated with NH3 was treated with RaNi (one spoonful, activated by washing with 1 l of abs EtOH) and hydrogenated in a Parr apparatus for 14 hours. The solution was filtered through celite and then through a millipore followed by evaporation of solvents in vacuo to give an oily solid. Trituration with EtOH afforded 8.2 g of crude white product: m.p. 187.5°-188.5°. Thin layer chromatography indicated an approximately 5% impurity (3% NH4OH - MeOH/silica gel). Dry column chromatography (1.5 g/400 g of silica gel--3% NH4OH/MeOH elluent) affords 4.8 g of pure N-[3-(2-aminoethyl)-1H-indol-5-yl]urea: m.p. 188.5°-189.5°; i.r. (KBr) 3400, 3360, 3280, 3200, and 1650 cm-1 ; nmr (d6 -DMSO) δ(TMS) 10.72 (1,S,indole NH), 8.37 (1,S,--NHCO--), 7.65 (1,d, Jmeta =2 Hz), 7.27 (1,d,Jortho =8 Hz), 7.10 (1,S,indole C2H), 7.02 (1,d of d, Jortho =8 Hz, Jmeta =2 Hz), 5.71 (2,S,--CONH2), 2.78 (4,S,--CH2CH2 --) and 2.30 ppm (2,S,--NH2).

Workup

  1. filtrationThe solution was filtered through celite
  2. customthrough a millipore followed by evaporation of solvents in vacuo
  3. customto give an oily solid
  4. customDry column chromatography (1.5 g/400 g of silica gel--3% NH4OH/MeOH elluent)

Sources & evidence

ORD record
ord-259bc865558b4e6b867de9f673816aab
Source dataset
uspto-grants-1989_02
Patent number
US04803218

Reaction notes

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