Tetrahydrofuran → HCID 12952716, compound

HRID 1263240Notes

Reaction equation

HRID 1263240 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][N:23]([N:26]=O)[CH2:22][CH2:21]2)=[CH:16][CH:15]=1.[OH-].[Na+]>O.C1C=CC=CC=1>[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([N:20]2[CH2:21][CH2:22][N:23]([NH2:26])[CH2:24][CH2:25]2)=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 1295271575051-59-1HCID 21226445Aluminium lithium hydride

Product 1

HCID 12952716HCID 12952716, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent2×

Procedure

To a stirred suspension of 10 parts of lithium aluminium hydride in 900 parts of tetrahydrofuran is added dropwise, during a 20 hours period, a solution of 40 parts of 1-(4-methoxyphenyl)-4-nitrosopiperazine in 720 parts of benzene. Upon completion, stirring is continued for 20 hours at room temperature. The reaction mixture is decomposed by the successive dropwise additions of 10 parts of water, 7.5 parts of a sodium hydroxide solution 50% and 30 parts of water. The whole is filtered and the filtrate is evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 1,1'-oxybisbutane. The product is filtered off and dried, yielding 18.56 parts of 4-(4-methoxyphenyl)-1-piperazinamine; mp. 107° C.

Workup

  1. additionis added dropwise, during a 20 hours period
  2. filtrationThe whole is filtered
  3. customthe filtrate is evaporated
  4. customThe residue is purified by column-chromatography over silica gel using
  5. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  6. customThe pure fractions are collected
  7. customthe eluent is evaporated
  8. customThe residue is crystallized from 1,1'-oxybisbutane
  9. filtrationThe product is filtered off
  10. customdried

Sources & evidence

ORD record
ord-38198bc6e95343638cc019a239144bfc
Source dataset
uspto-grants-1984_06
Patent number
US04456605

Reaction notes

Loading…