Tetrahydrofuran → HCID 15037539, compound

HRID 704742Notes

Reaction equation

HRID 704742 reaction equation
[AlH4-].[Li+].O1CCCC1.[NH:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[NH:17][CH:18]1[CH2:24][CH2:23][CH2:22][N:21]([C:25](OCC)=O)[CH2:20][CH2:19]1.[OH-].[Na+]>O.C(OCC)(=O)C>[CH3:25][N:21]1[CH2:22][CH2:23][CH2:24][CH:18]([NH:17][C:9]2[NH:8][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=2)[CH2:19][CH2:20]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 28112Lithium aluminum hydrideHCID 15037356HCID 15037356, compound

Product 1

HCID 15037539HCID 15037539, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred and heated (50° C.) mixture of 6.4 parts of lithium tetrahydroaluminate and 450 parts of tetrahydrofuran were added portionwise 23.5 parts of ethyl 4-(1H-benzimidazol-2-ylamino)hexahydro-1H-azepine-1-carboxylate under nitrogen atmosphere. Upon complete addition, stirring was continued for 2 hours at reflux temperature. The reaction mixture was decomposed with ethyl acetate, 30 parts of a sodium hydroxide solution and 30 parts of water. The whole was filtered over diatomaceous earth and the filtrate was evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 10.5 parts (55.0%) of N-(hexahydro-1-methyl-1H-azepin-4-yl)-1H-benzimidazol-2-amine; mp. 168.3° C. (compound 213).

Workup

  1. temperatureheated
  2. additionUpon complete addition
  3. stirringstirring
  4. temperatureat reflux temperature
  5. filtrationThe whole was filtered over diatomaceous earth
  6. customthe filtrate was evaporated
  7. customThe residue was crystallized from acetonitrile
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-82de43482b404c74bcc441e258126b02
Source dataset
uspto-grants-1991_01
Patent number
US04988689

Reaction notes

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