Water → HCID 14570270, compound

HRID 2286895Notes

Reaction equation

HRID 2286895 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:14][C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:4][CH2:3]1.C([Li])(C)(C)C.CO[NH2:28].O>CCCCCC.CCCCC>[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([NH2:28])[C:15]=3[O:14][C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 4113O-MethylhydroxylamineHCID 14570248HCID 14570248, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 14570270HCID 14570270, compound

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8058HexaneSolvent2×

Procedure

To a solution of 1'-methylxanthene-9-spiro-4'-piperidine (1.3 g.) in hexane (25 ml.) in an argon atmosphere is added a 1.6 molar solution of t-butyl lithium in pentane (3.5 ml.) with stirring at room temperature. The mixture is stirred for 1 hour at room temperature. Hydroxylamine methyl ether (0.4 g.) in hexane (5 ml.) is added dropwise during 5 minutes. Water is added and the organic layer separated, washed with water and dried with MgSO4. The solvent is evaporated to give a solid residue, which is recrystallised from hexane to give 1'-methyl-4-aminoxanthene-9-spiro-4'-piperidine, m.p. 173°-174° C. The above process is repeated using an equivalent amount of sulphur and paraformaldehyde as starting material in place of hydroxylamine methyl ether. The following compounds are thus prepared:

Workup

  1. stirringThe mixture is stirred for 1 hour at room temperature
  2. customthe organic layer separated
  3. washwashed with water
  4. dry with materialdried with MgSO4
  5. customThe solvent is evaporated
  6. customto give a solid residue, which
  7. customis recrystallised from hexane

Sources & evidence

ORD record
ord-437a16608ca94b1ca50748c989f9a0a8
Source dataset
uspto-grants-1981_05
Patent number
US04268514

Reaction notes

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