Sodium Carbonate → HCID 86751672, compound

HRID 2294902Notes

Reaction equation

HRID 2294902 reaction equation
Br.Br.C[N:4]([CH:15]1[CH2:20][CH2:19]NCC1)[C:5]1[S:6][C:7]2[CH:13]=[C:12]([OH:14])[CH:11]=[CH:10][C:8]=2[N:9]=1.[C:21](=[O:24])([O-:23])[O-].[Na+].[Na+].Cl[CH2:28][CH2:29][CH2:30][CH2:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=1>CN(C)C(=O)C>[C:12]([OH:14])(=[O:32])/[CH:13]=[CH:7]\[C:21]([OH:23])=[O:24].[F:39][C:36]1[CH:37]=[CH:38][C:33]([O:32][CH2:31][CH2:30][CH2:29][CH2:28][N:4]2[CH2:5][CH2:19][CH:20]([CH2:15][NH:4][C:5]3[S:6][C:7]4[CH:13]=[C:12]([OH:14])[CH:11]=[CH:10][C:8]=4[N:9]=3)[CH2:20][CH2:15]2)=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 21472462HCID 21472462, compoundHCID 21472464HCID 21472464, compound

Product 1

HCID 86751672HCID 86751672, compoundYield 117.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of 2-(methyl-4-piperidinylamino)-6-benzothiazolol dihydrobromide (0.056 mol) and sodium carbonate (0.142 mol) in N,N-dimethylacetamide (500 ml) was stirred for 1 hour at 60° C. A solution of 1-(4-chlorobutoxy)-4-fluorobenzene (0.061 mol) in N,N-dimethylacetamide (15 ml) was added and the reaction mixture was stirred overnight at 60° C. The cooled reaction mixture was poured out into ice water. This mixture was extracted with toluene. The separated organic layer was dried (MgSO4), filtered and the solvent was evaporated. The residue (30 g) was purified by column chromatography over silica gel (eluent: CH2 Cl2 /CH3OH 97/3). The pure fractions were collected and the solvent was evaporated. The residue was converted into the (Z)-2-butenedioic acid salt (1:1) in 2-propanol. The precipitate was filtered off and dried, yielding 18 g (58.9%)of 2-[[1-[4-(4-fluorophenoxy)butyl]-4-piperidinyl]methylamino]-6-benzothiazolol (Z)-2-butenedioate(1:1); mp. 180.7° C. (comp. 4).

Workup

  1. stirringthe reaction mixture was stirred overnight at 60° C
  2. customThe cooled reaction mixture
  3. extractionThis mixture was extracted with toluene
  4. dry with materialThe separated organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue (30 g) was purified by column chromatography over silica gel (eluent: CH2 Cl2 /CH3OH 97/3)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated
  10. filtrationThe precipitate was filtered off
  11. customdried

Sources & evidence

ORD record
ord-5b4c7bd2be074ef18779d4f5838a5008
Source dataset
uspto-grants-1997_11
Patent number
US05691354

Reaction notes

Loading…