Diethyl Ether → HCID 21971879, compound

HRID 369070Notes

Reaction equation

HRID 369070 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.[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1.C(OCC)C>ClCCl>[Cl:27][C:24]1[CH:25]=[CH:26][C:20]2[O:19][CH2:18][C@H:17]([CH2:16][N:13]3[CH2:14][CH2:15][CH:10]([CH2:9][NH:8][S:36]([C:33]4[CH:32]=[CH:31][C:30]([O:29][CH3:28])=[CH:35][CH:34]=4)(=[O:38])=[O:37])[CH2:11][CH2:12]3)[O:22][C:21]=2[CH:23]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 11000970HCID 11000970, compound

Product 1

HCID 21971879HCID 21971879, compoundYield 28.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (0.62 ml) was added to a solution of (S)-4-(aminomethyl)-1-(7-chloro-1,4-benzodioxan-2-ylmethyl)piperidine (0.44 g) and 4-methoxybenzene-sulphonyl chloride (0.61 g) in dichloromethane (22 ml) under nitrogen. The reaction 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 20:1 mixture of dichloromethane and methanol gave a colourless gum. Trituration with diethyl ether (20 ml) yielded (S)-(-)-N-{[1-(7-chloro-1,4-benzodioxan-2-ylmethyl)-4-piperidyl]-methyl}-4-methoxybenzenesulphonamide as a white solid (0.20 g); m.p. 130-131° C., [α]D22.5 28.9° (c=0.51, CH2Cl2).

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 20:1 mixture of dichloromethane and methanol
  7. customgave a colourless gum

Sources & evidence

ORD record
ord-5ef8bb81794c40179fda4414f2219810
Source dataset
uspto-grants-2000_10
Patent number
US06136825

Reaction notes

Loading…