1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → n-Tert-butyldimethylsiloxy-1-[4-(4-chlorophenyl)piperazine-1-sulfonyl]piperidine-2-(rs)-carboxamide

HRID 609683Notes

Reaction equation

HRID 609683 reaction equation
[Si:1]([O:8][NH2:9])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][N:32]([S:35]([N:38]3[CH2:43][CH2:42][CH2:41][CH2:40][CH:39]3[C:44](O)=[O:45])(=[O:37])=[O:36])[CH2:31][CH2:30]2)=[CH:25][CH:24]=1>C(Cl)Cl>[O:8]([NH:9][C:44]([CH:39]1[CH2:40][CH2:41][CH2:42][CH2:43][N:38]1[S:35]([N:32]1[CH2:33][CH2:34][N:29]([C:26]2[CH:25]=[CH:24][C:23]([Cl:22])=[CH:28][CH:27]=2)[CH2:30][CH2:31]1)(=[O:37])=[O:36])=[O:45])[Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 4691350O-(tert-Butyldimethylsilyl)hydroxylamineHCID 226157981-[4-(4-Chlorophenyl)piperazine-1-sulfonyl]piperidine-2-(rs)-carboxylic acid

Product 1

HCID 22615606n-Tert-butyldimethylsiloxy-1-[4-(4-chlorophenyl)piperazine-1-sulfonyl]piperidine-2-(rs)-carboxamideYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

O-(tert-butyldimethylsilyl)hydroxylamine (57 mg, 0.39 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (59 mg, 0.31 mmol) were added to a solution of 1-[4-(4-chlorophenyl)piperazine-1-sulfonyl]piperidine-2-(RS)-carboxylic acid (100 mg, 0.26 mmol), [prepared as described above] in methylene chloride (4 ml). The reaction mixture was stirred overnight at RT and then diluted with methylene chloride. The solution was washed with water, 10% citric acid, and brine, and dried over MgSO4. After the organics were removed the residue was chromatographed (SiO2, 20-30% ethyl acetate/hexane) to give N-tert-butyldimethylsiloxy-1-[4-(4-chlorophenyl)piperazine-1-sulfonyl]piperidine-2-(RS)-carboxamide as a colorless foam (56%).

Workup

  1. washThe solution was washed with water, 10% citric acid, and brine
  2. dry with materialdried over MgSO4
  3. customAfter the organics were removed the residue
  4. customwas chromatographed (SiO2, 20-30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-16a0eee8828a4790b5a93a7e5128aab3
Source dataset
uspto-grants-1999_12
Patent number
US05998412

Reaction notes

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