Triethylamine → 4-[[[(6-Hydroxyhexyl)amino]-carbonyl]oxy]-1-piperidinecarboxylic acid 4-phenoxyphenyl ester

HRID 618287Notes

Reaction equation

HRID 618287 reaction equation
C(N(CC)CC)C.[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15].[O:16]([C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30]([N:32]2[CH2:37][CH2:36][CH:35]([O:38][C:39](OC3C=CC([N+]([O-])=O)=CC=3)=[O:40])[CH2:34][CH2:33]2)=[O:31])=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl>[O:16]([C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30]([N:32]2[CH2:33][CH2:34][CH:35]([O:38][C:39]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])=[O:40])[CH2:36][CH2:37]2)=[O:31])=[CH:25][CH:24]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199606-Amino-1-hexanolHCID 54469753HCID 54469753, compound

Product 1

HCID 537895824-[[[(6-Hydroxyhexyl)amino]-carbonyl]oxy]-1-piperidinecarboxylic acid 4-phenoxyphenyl esterYield 114.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of triethylamine (65.5 mL, 0.47 mol) and 6-aminohexanol (13.2 g, 0.11 mol) in 300 mL of methylene chloride was added dropwise under nitrogen to a solution of the carbonate (45.0 g, 0.09 mol) produced in Example 3 in 500 mL of methylene chloride at room temperature. After the addition the solution was stirred at room temperature overnight. The reaction was extracted one time with 1N HCl and then multiple times with saturated Na2CO3, dried (MgSO4) and the solvent removed under reduced pressure to give 47.0 g of an off-white solid. Recrystallization from methylene chloride-diisopropyl ether gave 35.5 g (83%) of the title compound as a white crystalline solid, mp 69-72° C.

Workup

  1. additionAfter the addition the solution
  2. extractionThe reaction was extracted one time with 1N HCl
  3. dry with materialmultiple times with saturated Na2CO3, dried (MgSO4)
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-70cd0b67a5354b49a9e0e56896c3a9d8
Source dataset
uspto-grants-1999_09
Patent number
US05952354

Reaction notes

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