Sodium Carbonate → HCID 13588109, compound

HRID 620512Notes

Reaction equation

HRID 620512 reaction equation
Br.Br[CH2:3][CH2:4][CH2:5][NH2:6].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]=[C:16]2[NH:24][CH:25]2[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][N:33]=[C:34]=[S:35])[CH2:27][CH2:26]2)=[CH:10][CH:9]=1.C(=O)([O-])[O-:37].[Na+].[Na+]>O1CCCC1>[OH2:37].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]=[C:16]2[NH:24][CH:25]2[CH2:26][CH2:27][N:28]([CH2:31][CH2:32][NH:33][C:34]3[S:35][CH2:3][CH2:4][CH2:5][N:6]=3)[CH2:29][CH2:30]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 787013-Bromopropylamine hydrobromideHCID 128917531-(4-fluorophenylmethyl)-N-[1-(2-isothiocyanatoethyl)-4-piperidinyl]1H-benzimidazol-2-amine

Product 1

HCID 13588109HCID 13588109, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2.2 parts of 3-bromo-1-propanamine hydrobromide, 4.1 parts of 1-[(4-fluorophenyl)methyl]-N-[1-(2-isothiocyanatoethyl)-4-piperidinyl]-1H-benzimidazol-2-amine, 2.2 parts of sodium carbonate and 135 parts of tetrahydrofuran was stirred overnight at room temperature. The reaction mixture was further stirred and refluxed for 3 hours. The mixture was filtered and the filtrate was evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume), saturated with ammonia, as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile, yielding 2.5 parts of 1-[(4-fluoro-phenyl)methyl]-N-[1-[2-[(5,6-dihydro-4H-1,3-thiazin-2-yl)amino]ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine monohydrate; mp. 121.4° C. (compound 117).

Workup

  1. stirringThe reaction mixture was further stirred
  2. temperaturerefluxed for 3 hours
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated
  5. customThe residue was purified by column-chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol (95:5 by volume)
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-25bff476ee614dc5ac3ac431a70a423c
Source dataset
uspto-grants-1989_04
Patent number
US04820822

Reaction notes

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