Water → HCID 22004688, compound

HRID 324384Notes

Reaction equation

HRID 324384 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.C([N:18]([CH2:21][CH3:22])CC)C.C(N[C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1)(=O)C.[OH2:37]>ClCCl>[C:21]([NH:18][C:3]1([CH2:2][NH:1][S:33]([C:30]2[CH:31]=[CH:32][CH:27]=[CH:28][CH:29]=2)(=[O:35])=[O:34])[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)(=[O:37])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 8481N-Acetylsulfanilyl chlorideHCID 7368171-Boc-4-(aminomethyl)piperidine

Product 1

HCID 22004688HCID 22004688, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 4-(aminomethyl)-1-(tert-butoxycarbonyl)piperidine (5.20 g) in dichloromethane (100 ml) was treated with triethylamine (5.31 g) and then 4-acetamidobenzenesulphonyl chloride (6.07 g) was added in small portions. The mixture was stirred at room temperature for 4 hours and then left to stand for 72 hours. The mixture was poured into water (200 ml) and extracted with dichloromethane (150 ml). The organic solution was washed with hydrochloric acid (1M;100 ml) which led to precipitation of a pale-yellow solid. The solid was collected by filtration, dissolved in industrial methylated spirit (300 ml), dried over sodium sulphate and evaporated under reduced pressure to give N-{[4-acetamido-1-(tert-butoxycarbonyl)-4-piperidyl]methyl}benzenesulphonamide (3.72 g) as a pale-yellow solid, m.p. 226-7° C.

Workup

  1. waitleft
  2. waitto stand for 72 hours
  3. extractionextracted with dichloromethane (150 ml)
  4. washThe organic solution was washed with hydrochloric acid (1M;100 ml) which
  5. customled to precipitation of a pale-yellow solid
  6. filtrationThe solid was collected by filtration
  7. dissolutiondissolved in industrial methylated spirit (300 ml)
  8. dry with materialdried over sodium sulphate
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-70fed309f94d4742b19d4b197c0a9f2d
Source dataset
uspto-grants-2001_04
Patent number
US06218405B1

Reaction notes

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