Water → 1-(t-Butoxycarbonyl)4-(1-(6-chloronaphth-2-ylsulphonyl)piperazin-4-ylcarbonyl)piperidine

HRID 2288729Notes

Reaction equation

HRID 2288729 reaction equation
C(N(CC)CC)C.Cl.[Cl:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([S:20]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)(=[O:22])=[O:21])[CH:14]=[CH:13]2.[C:29]([O:33][C:34]([N:36]1[CH2:41][CH2:40][CH:39]([C:42](ON2C(=O)CCC2=O)=[O:43])[CH2:38][CH2:37]1)=[O:35])([CH3:32])([CH3:31])[CH3:30].O>ClCCl.C(OCC)(=O)C>[C:29]([O:33][C:34]([N:36]1[CH2:41][CH2:40][CH:39]([C:42]([N:26]2[CH2:25][CH2:24][N:23]([S:20]([C:15]3[CH:14]=[CH:13][C:12]4[C:17](=[CH:18][CH:19]=[C:10]([Cl:9])[CH:11]=4)[CH:16]=3)(=[O:21])=[O:22])[CH2:28][CH2:27]2)=[O:43])[CH2:38][CH2:37]1)=[O:35])([CH3:32])([CH3:31])[CH3:30]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 15578030Succinimido 1-t-butoxycarbonylpiperidine-4-carboxylateHCID 227097661-(6-Chloronaphth-2-ylsulphonyl)piperazine hydrochloride

Product 1

HCID 121120201-(t-Butoxycarbonyl)4-(1-(6-chloronaphth-2-ylsulphonyl)piperazin-4-ylcarbonyl)piperidineYield 81%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (2.92 ml) was added to a mixture of 1-(6-chloronaphth-2-ylsulphonyl)piperazine hydrochloride (6.93 g) in dichloromethane (100 ml). 1-(1-(t-butoxycarbonyl)piperidin-4-ylcarbonyloxy)-2,5-dioxopyrrolidine (6.25 g) was added and the mixture stirred overnight. The mixture was evaporated to give a solid which was suspended in ethyl acetate (200 ml). Water (50 ml) was added and the ethyl acetate phase separated, washed with water (4×50 ml), brine (50 ml), dried (MgSO4) and evaporated. The residue was purified by flash chromatography on silica gel using a 75:25 mixture of ethyl acetate/hexane as eluent to give 1-(t-butoxycarbonyl)-4-(1-(6-chloronaphth-2-ylsulphonyl)piperazin-4-ylcarbonyl)piperidine (8.1 g);

Workup

  1. customThe mixture was evaporated
  2. customto give a solid which
  3. customthe ethyl acetate phase separated
  4. washwashed with water (4×50 ml), brine (50 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by flash chromatography on silica gel using
  8. additiona 75:25 mixture of ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-2016414e00734b129bf01f4b014f0f99
Source dataset
uspto-grants-2000_07
Patent number
US06090813

Reaction notes

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