Diethyl Ether → HCID 53864197, compound

HRID 369069Notes

Reaction equation

HRID 369069 reaction equation
C(N(CC)CC)C.[NH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C@@H:17]2[O:22][C:21]3[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:20]=3[O:19][CH2:18]2)[CH2:12][CH2:11]1.[C:28]([NH:31][C:32]1[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1)(=[O:30])[CH3:29].C(OCC)C>ClCCl>[C:28]([NH:31][C:32]1[CH:33]=[CH:34][C:35]([S:38]([NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][C@@H:17]3[O:22][C:21]4[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:20]=4[O:19][CH2:18]3)[CH2:12][CH2:11]2)(=[O:40])=[O:39])=[CH:36][CH:37]=1)(=[O:30])[CH3:29]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 8481N-Acetylsulfanilyl chlorideHCID 11000970HCID 11000970, compound

Product 1

HCID 53864197HCID 53864197, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (0.62 ml) was added to a cloudy solution of (S)-4-(aminomethyl)-1-(7-chloro-1,4-benzodioxan-2-ylmethyl)piperidine (0.44 g) and 4-acetamidobenzenesulphonyl chloride (0.65 g) in dichloromethane (22 ml) under nitrogen. The resulting solution was stirred for 20 hours, diluted with dichloromethane (100 ml) and washed with water (100 ml) and brine (100 ml). After drying over anhydrous magnesium sulphate, the mixture was concentrated under reduced pressure to afford an orange oil. Purification by flash chromatography on silica gel eluting with a 15:1 mixture of dichloromethane and methanol gave an orange gum. Trituration with diethyl ether (20 ml) yielded (S)-(-)-4-acetamido-N-{[1-(7-chloro-1,4-benzodioxan-2-ylmethyl)-4-piperidyl]methyl}benzenesulphonamide as a pale orange solid (0.34 g); m.p. 173-176° C., [α]D22 -39.3° (c=0.37, MeOH).

Workup

  1. washwashed with water (100 ml) and brine (100 ml)
  2. dry with materialAfter drying over anhydrous magnesium sulphate
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customto afford an orange oil
  5. customPurification by flash chromatography on silica gel eluting
  6. additionwith a 15:1 mixture of dichloromethane and methanol
  7. customgave an orange gum

Sources & evidence

ORD record
ord-f9ce4398e9ca415ca68ff9d196c046cb
Source dataset
uspto-grants-2000_10
Patent number
US06136825

Reaction notes

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