Sodium Carbonate → N-[[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]methyl]thiazolo[4,5-c]pyridin-2-amine

HRID 1789514Notes

Reaction equation

HRID 1789514 reaction equation
Br.Br.[O:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH2:5][CH:4]1[CH2:13][N:14]1[CH2:19][CH2:18][CH:17]([CH2:20][NH2:21])[CH2:16][CH2:15]1.CS([C:26]1[S:27][C:28]2[CH:33]=[CH:32][N:31]=[CH:30][C:29]=2[N:34]=1)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C(=O)C>[O:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH2:5][CH:4]1[CH2:13][N:14]1[CH2:15][CH2:16][CH:17]([CH2:20][NH:21][C:26]2[S:27][C:28]3[CH:33]=[CH:32][N:31]=[CH:30][C:29]=3[N:34]=2)[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 140490391-[(2,3-Dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinemethanamine dihydrobromideHCID 157251382-(Methylsulfonyl)thiazolo[4,5-c]pyridine

Product 1

HCID 15611599N-[[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]methyl]thiazolo[4,5-c]pyridin-2-amineYield 20%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 6.7 parts of 1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinemethanamine dihydrobromide, 3.26 parts of 2-(methylsulfonyl)thiazolo[4,5-c]pyridine, 4.25 parts of sodium carbonate and 18 parts of N,N-dimethylacetamide was stirred for 2 hours at 150° C. The reaction mixture was poured into ice water. The product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (97:3 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 1,1'-oxybisethane. The product was filtered off and dried, yielding 1.15 parts (20%) of N-[[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]methyl]thiazolo[4,5-c]pyridin-2-amine; mp. 147.1° C. (compound 58).

Workup

  1. extractionThe product was extracted with 4-methyl-2-pentanone
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol (97:3 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. customThe residue was crystallized from 1,1'-oxybisethane
  10. filtrationThe product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-0701af8e90954ddcb99b613811caad29
Source dataset
uspto-grants-1987_08
Patent number
US04689330

Reaction notes

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