Cyclohexylamine → HCID 53771590, compound

HRID 260338Notes

Reaction equation

HRID 260338 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[O:15]([C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]([NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][O:38][C:39]([N:41]2[CH2:46][CH2:45][CH:44]([O:47][C:48](OC3C=CC([N+]([O-])=O)=CC=3)=[O:49])[CH2:43][CH2:42]2)=[O:40])=[O:30])=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl>[O:15]([C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]([NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][O:38][C:39]([N:41]2[CH2:46][CH2:45][CH:44]([O:47][C:48](=[O:49])[NH:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH2:43][CH2:42]2)=[O:40])=[O:30])=[CH:24][CH:23]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 8471TriethylamineHCID 152933074-(4-Nitro-phenoxycarbonyloxy)-piperidine-1-carboxylic acid 6-[(4-phenoxy-phenyl)-oxycarbonylamino]-hexyl ester

Product 1

HCID 53771590HCID 53771590, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of cyclohexylamine (442 mg, 3.86 mmol) and triethylamine (2.24 mL, 16.1 mmol) in 30 mL of methylene chloride was added under nitrogen dropwise to a solution of the carbonate prepared in Example 5 (2.0 g, 3.22 mmol) in 30 mL of methylene chloride at ice bath temperature. After the addition the cooling bath was removed and the reaction stirred at room temperature for approximately 48 hours. The reaction mixture was extracted one time with 1N HCl, multiple times with saturated Na2CO3, dried (MgSO4) and the solvent removed under reduced pressure to give 1.92 g of a waxy yellow solid. Purification of the solid on silica gel (230-400 mesh) using 20% ethyl acetate-methylene chloride as the eluent gave 884 mg (47%) of the title compound as a white crystalline solid, mp 138°-142° C.

Workup

  1. additionAfter the addition the cooling bath
  2. customwas removed
  3. extractionThe reaction mixture was extracted one time with 1N HCl, multiple times with saturated Na2CO3
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-2c5a12ab84644af4be265918010c200b
Source dataset
uspto-grants-1996_06
Patent number
US05527804

Reaction notes

Loading…