Dimethylformamide → HCID 13016615, compound

HRID 127269

Reaction equation

HRID 127269 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[O:13]1[C:17]2([CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH2:16][NH:15][C:14]1=[O:23].C(N(CC)CC)C.CN(C)C=O>O>[NH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([CH2:3][CH2:2][N:20]2[CH2:19][CH2:18][C:17]3([O:13][C:14](=[O:23])[NH:15][CH2:16]3)[CH2:22][CH2:21]2)=[CH:5]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 769243-(2-Bromoethyl)indoleHCID 129541141-Oxa-3,8-diazaspiro(4.5)decan 2-one

Product 1

HCID 13016615HCID 13016615, compoundYield 44.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.94 g of 3-(2-bromoethyl)indole, 2.74 g of 1-oxa-3,8-diazaspiro[4.5]decan-2-one, 2 g of triethylamine and 10 ml N,N-dimethylformamide is stirred at 50° for 16 hours. The mixture is cooled to room temperature and 150 ml of water is added with stirring The aqueous layer is decanted from the residue which adheres to the walls of the flask. The residue is washed with 100 ml water following by 100 ml diethyl ether. The residue is dissolved in a minimum amount of 10% (v/v) methanol-dichloromethane and the resulting solution is filtered through 25 g silica gel with 150 ml of 10% (v/v) methanol-dichloromethane. Evaporation of the filtrate followed by crystallization with diethyl ether affords 2.35 g of 8-[2-(3-indolyl)ethyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one, mp 183°-186° (d).

Workup

  1. stirringwith stirring The aqueous layer
  2. customis decanted from the residue which
  3. washThe residue is washed with 100 ml water following by 100 ml diethyl ether
  4. dissolutionThe residue is dissolved in a minimum amount of 10% (v/v) methanol-dichloromethane
  5. filtrationthe resulting solution is filtered through 25 g silica gel with 150 ml of 10% (v/v) methanol-dichloromethane
  6. customEvaporation of the filtrate
  7. customfollowed by crystallization with diethyl ether

Sources & evidence

ORD record
ord-60cf503172914728bf83ac105a88ff04
Source dataset
uspto-grants-1981_03
Patent number
US04255432

Linked notes

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