Triethylamine → 4-(6-Hydroxy-hexylcarbamoyloxy)-piperidine-1-carboxylic acid benzyl ester

HRID 618294Notes

Reaction equation

HRID 618294 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:18]([O:20]C2C=CC([N+]([O-])=O)=CC=2)=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][OH:37].C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([O:17][C:18](=[O:20])[NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][OH:37])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 199606-Amino-1-hexanol2×HCID 543969734-(4-Nitro-phenoxycarbonyloxy)-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 540795684-(6-Hydroxy-hexylcarbamoyloxy)-piperidine-1-carboxylic acid benzyl esterYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the carbonate (128.826 g, 0.322 moles) produced in Example 21 in 450 ml of methylene chloride was added dropwise under nitrogen to a solution of 6-amino-1-hexanol (56.6 g, 0.483 moles) and triethylamine (224.2 ml, 1.61 moles) in 2 L of methylene chloride at room temperature. After the addition the reaction was stirred overnight at room temperature. By TLC the reaction was not complete. An additional 37.7 g (0.322 moles) of 6-amino-1-hexanol and 224.2 ml (1.61 moles) of triethylamine were added and the stirring continued overnight. By TLC the reaction was complete. The reaction was extracted two times with 1N HCl, multiple times with saturated Na2CO3, dried (MgSO4) and the solvent removed under reduced pressure to give 95.0 g (78%) of a yellow oil which crystallized on standing, mp 50-52° C.

Workup

  1. additionAfter the addition the reaction
  2. customthe stirring continued overnight
  3. extractionThe reaction was extracted two times 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-17abec915e82483eb364b34536489ae7
Source dataset
uspto-grants-1999_09
Patent number
US05952354

Reaction notes

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