Tetrahydrofuran → HCID 86591407, compound

HRID 1677816Notes

Reaction equation

HRID 1677816 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([N:19]3[CH2:28][CH2:27][C:22]4(OCC[O:23]4)[CH2:21][CH2:20]3)(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1.C1COCC1>Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([S:16]([N:19]3[CH2:20][CH2:21][C:22](=[O:23])[CH2:27][CH2:28]3)(=[O:17])=[O:18])=[CH:14][CH:15]=2)=[O:7])=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 86591406HCID 86591406, compound

Product 1

HCID 86591407HCID 86591407, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4-chloro-N-[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-ylsulfonyl)benzyl]benzamide 7c (2.7 g, 5.99 mmol) was suspended in 6 N HCl (40 ml) and THF added until a clear solution was obtained (about 40 ml). The reaction mixture was stirred at room temp overnight and THF was removed in vacuo. The resulting suspension was diluted with cold water (50 ml), aged for 1 h at room temp and filtered. The filter residue was dried under high vacuum for several hours to yield 2.0 g (82%) of ketone 4-chloro-N-{4-[(4-oxo-1-piperidinyl)sulfonyl]benzyl}benzamide 7d as colourless powder in >90% purity (LC-MS).

Workup

  1. customwas obtained (about 40 ml)
  2. customTHF was removed in vacuo
  3. additionThe resulting suspension was diluted with cold water (50 ml)
  4. waitaged for 1 h at room temp
  5. filtrationfiltered
  6. customThe filter residue was dried under high vacuum for several hours

Sources & evidence

ORD record
ord-75a1b8b1197040109ac050cd606037d2
Source dataset
uspto-grants-2011_08
Patent number
US08008341B2

Reaction notes

Loading…