Formic Acid → HCID 14349072, compound

HRID 346068Notes

Reaction equation

HRID 346068 reaction equation
[CH3:1][O:2][C:3]1[C:21]([O:22][CH3:23])=[CH:20][C:6]2[CH:7]([O:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=1.C=[O:25].[CH:26]([OH:28])=[O:27]>O.C(=O)([O-])[O-].[Na+].[Na+]>[C:21]([OH:22])(=[O:25])/[CH:20]=[CH:6]\[C:26]([OH:28])=[O:27].[CH3:1][O:2][C:3]1[C:21]([O:22][CH3:23])=[CH:20][C:6]2[CH:7]([O:12][C:13]3[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=3)[CH2:8][N:9]([CH3:26])[CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 14349069HCID 14349069, compound

Product 1

HCID 14349072HCID 14349072, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
75 °C

Procedure

7,8-Dimethoxy-1-(4-fluorophenoxy)-2,3,4,5-tetrahydro-3-benzazepine (3.5 g, 11 m mole) of Example 42 was dissolved in 9 ml 95% formic acid and to this was added 8 ml 37% formaldehyde solution. The mixture was stirred at 75° C. for one hour, then was cooled, diluted with water and basified with sodium carbonate. The oil which separated was extracted with ether then was washed with water, dried (saturated NaCl, anhydrous MgSO4), filtered and evaporated to an oil. The oil was converted as in Example 42 to the maleate salt (3.7 g, mp 124°-135° C.). This material was recrystallized twice from isopropanol to yield 2.7 g (55%) of 7,8-dimethoxy-1-(4-fluorophenoxy)-3-methyl-2,3,4,5-tetrahydro-3-benzazepine maleate d 152°-153° C.

Workup

  1. temperaturewas cooled
  2. customThe oil which separated
  3. extractionwas extracted with ether
  4. washthen was washed with water
  5. dry with materialdried (saturated NaCl, anhydrous MgSO4)
  6. filtrationfiltered
  7. customevaporated to an oil
  8. customThis material was recrystallized twice from isopropanol

Sources & evidence

ORD record
ord-c6f66d1df5394f8a8c247bb2c0fe366c
Source dataset
uspto-grants-1991_10
Patent number
US05059688

Reaction notes

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