Water → 6'-hydroxyspiro(9H-fluorene-9,3'-piperidine)-2'-one

HRID 1153872Notes

Reaction equation

HRID 1153872 reaction equation
[OH-:1].[CH2:2]([N+](C)(C)C)[C:3]1[CH:8]=CC=CC=1.[C:13]([CH:16]1[C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)(=[O:15])[NH2:14].O>C(#N)C>[OH:1][CH:2]1[NH:14][C:13](=[O:15])[C:16]2([C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:22]3[C:17]2=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:8][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 66854Benzyltrimethylammonium hydroxideHCID 3450289H-fluorene-9-carboxamide

Product 1

HCID 133680416'-hydroxyspiro(9H-fluorene-9,3'-piperidine)-2'-oneYield 89%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

The general procedure of Example 1 was again followed when a solution of N-benzyltrimethylammonium hydroxide (Triton B) which is a 40% methanolic solution (3.5 ml) in acetonitrile (10 ml) was added dropwise over 0.25 hour to a suspension of 9-carbamoylfluorene (20.9 g) in acetonitrile (100 ml) keeping the temperature below 25° C. The reaction mixture was stirred at room temperature for 2 hours. Water (300 ml) was then added slowly over 1 hour and the crystallized product was isolated by filtration, washed with water and dried in vacuo overnight at 50° C. to give 89% yield of 6'-hydroxyspiro(9H-fluorene-9,3'-piperidine)-2'-one melting at 201°-205° C. (decomp). The product was identical spectroscopically to that prepared in Example 1.

Workup

  1. customthe temperature below 25° C
  2. customthe crystallized product was isolated by filtration
  3. washwashed with water
  4. customdried in vacuo overnight at 50° C.

Sources & evidence

ORD record
ord-bffc2806517a44c7995bd6155751815f
Source dataset
uspto-grants-1984_12
Patent number
US04486592

Reaction notes

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