Water → HCID 20537368, compound

HRID 1155655Notes

Reaction equation

HRID 1155655 reaction equation
[O:1]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:5][NH:4][C:3](=[O:12])[CH2:2]1.Br[CH2:14][CH2:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[NH:18][CH:17]=1.O>CN(C)C=O.C(N(CC)CC)C>[NH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]([CH2:15][CH2:14][N:9]2[CH2:8][CH2:7][C:6]3([O:1][CH2:2][C:3](=[O:12])[NH:4][CH2:5]3)[CH2:11][CH2:10]2)=[CH:17]1

Participants

6

Reactant 3

HCID 962WaterHCID 769243-(2-Bromoethyl)indoleHCID 130594341-Oxa-4,9-diazaspiro(5.5)undecan-3-one

Product 1

HCID 20537368HCID 20537368, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A solution of the hydrobromide salt of 1-oxa-4,9-diazaspiro[5.5]undecan-3-one (15 g) and 3-(2-bromoethyl)indole (13.5 g) in 75 ml of dimethylformamide and 20 ml of triethylamine was stirred at 65° C. for 16 hours. Water was added and the mixture was extracted with methylene chloride. The organic layer was extracted with 5% hydrochloric acid and the aqueous layer was made basic with ammonium hydroxide and extracted with methylene chloride. Evaporation left a residue which was chromatographed on silica gel with 10% methanol-methylene chloride to give 8.0 g of 9-[2-(3-indolyl)ethyl-]-1-oxa-4,9-diazaspiro[5.5] undecan-3-one as the free base, mp 48°-50° C. The free base was dissolved in methanol and acidified with methanolic hydrochloric acid. The precipitate was washed with ether to give 7 g of the hydrochloride salt of 9-[2-(3-indolyl)ethyl]-1-oxa-4,9-diazaspiro[5.5]undecan-3-one, mp 272°-275° C. (dec).

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. extractionThe organic layer was extracted with 5% hydrochloric acid
  3. extractionextracted with methylene chloride
  4. customEvaporation
  5. waitleft a residue which
  6. customwas chromatographed on silica gel with 10% methanol-methylene chloride

Sources & evidence

ORD record
ord-d9805cea9e6e49fc9edc6c1bb6bb5de6
Source dataset
uspto-grants-1982_06
Patent number
US04332804

Reaction notes

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