Ammonia → HCID 21527602, compound

HRID 1658484Notes

Reaction equation

HRID 1658484 reaction equation
[CH2:1]([NH:4][CH2:5][CH:6]([OH:19])[CH2:7][O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][C:12](=[O:18])[NH:13]2)[CH:2]=[CH2:3].Cl.[C:21]12([C:31](Cl)=[O:32])[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]3)[CH2:22]1)[CH2:28]2.N>CN(C)P(=O)(N(C)C)N(C)C.O>[C:21]12([C:31]([O:19][CH:6]([CH2:5][NH:4][CH2:1][CH:2]=[CH2:3])[CH2:7][O:8][C:9]3[CH:17]=[CH:16][CH:15]=[C:14]4[C:10]=3[CH2:11][C:12](=[O:18])[NH:13]4)=[O:32])[CH2:28][CH:27]3[CH2:26][CH:25]([CH2:24][CH:23]([CH2:29]3)[CH2:22]1)[CH2:30]2

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 989151-Adamantanecarbonyl chlorideHCID 21527620HCID 21527620, compound

Product 1

HCID 21527602HCID 21527602, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

1.35 g of 4-(3-allylamino-2-hydroxypropoxy)oxindole are converted into the hydrochloride, are then dissolved in 15 cc of hexamethyl-phosphoric acid triamide and allowed to stand at room temperature for 70 hours with 1.45 g of adamantane-1-carboxylic acid chloride. The mixture is poured into water, is rendered alkaline with a 10% ammonia solution and is extracted with methylene chloride. The evaporation residue of the methylene chloride phase is chromatographed on silica gel with methylene chloride and 1% of methanol, and the resulting title compound is converted into its hydrogen oxalate. M.P. 170°-172° from ethanol.

Workup

  1. extractionis extracted with methylene chloride
  2. customThe evaporation residue of the methylene chloride phase is chromatographed on silica gel with methylene chloride and 1% of methanol

Sources & evidence

ORD record
ord-273a13e39599489f9a88fdcca0db0dde
Source dataset
uspto-grants-1976_06
Patent number
US03965095

Reaction notes

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