Phenyl glycidyl ether → 1'-(2-Hydroxy-3-phenoxypropyl)-1-methyl-2-oxo-indoline-3-spiro-4'-piperidine

HRID 224614Notes

Reaction equation

HRID 224614 reaction equation
[O:1]([CH2:8][CH:9]1[O:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:12][N:13]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:15]2([CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[C:14]1=[O:27]>C(O)C>[OH:11][CH:9]([CH2:8][O:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:10][N:18]1[CH2:19][CH2:20][C:15]2([C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:13]([CH3:12])[C:14]2=[O:27])[CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 31217Phenyl glycidyl etherHCID 215841551-Methylspiro[indoline-3,4'-piperidin]-2-one

Product 1

HCID 705924761'-(2-Hydroxy-3-phenoxypropyl)-1-methyl-2-oxo-indoline-3-spiro-4'-piperidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.7 g of 1-phenoxy-2,3-epoxypropane, 2 g of 1-methyl-2-oxo-indoline-3-spiro-4'-piperidine and 120 ml of ethanol was refluxed for 3 hours. The resulting mixture was concentrated and crystallized from diisopropylether to give 1'-(2-hydroxy-3-phenoxypropyl)-1-methyl-2-oxo-indoline-3-spiro-4'-piperidine

Workup

  1. temperaturewas refluxed for 3 hours
  2. concentrationThe resulting mixture was concentrated
  3. customcrystallized from diisopropylether

Sources & evidence

ORD record
ord-f009d0cab4cd42a8b14df80ecf9c6b1f
Source dataset
uspto-grants-1980_11
Patent number
US04233307

Reaction notes

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