Water → Benzyl 4-(3-hydroxypropyl)piperidine-1-carboxylate

HRID 280974Notes

Reaction equation

HRID 280974 reaction equation
O.[CH2:2]([O:9][C:10](Cl)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH:13]1[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][CH2:21][OH:22])[CH2:15][CH2:14]1.C(N(CC)CC)C>C(Cl)Cl>[CH2:2]([O:9][C:10]([N:13]1[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][CH2:21][OH:22])[CH2:15][CH2:14]1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 814974-Piperidinepropanol

Product 1

HCID 14989193Benzyl 4-(3-hydroxypropyl)piperidine-1-carboxylateYield 67.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of methylene chloride (400 ml) and water (40 ml) are added dropwise benzyloxycarbonyl chloride (100 g) and a solution of 3-(4-piperidyl)propanol (84 g) and triethylamine (65 g) in methylene chloride (100 ml) for 45 minutes at room temperature. After addition is completed, stirring is continued for further 1 hour. The methylene chloride layer is separated, washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Vacuum distillation of the oily residue is carried out to remove the low boiling material (50°-60° C./5 mmHg). 3-(1-Benzyloxycarbonyl-4-piperidyl)propanol (110 g) is obtained as a yellow oily residue.

Workup

  1. additionAfter addition
  2. customThe methylene chloride layer is separated
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. distillationVacuum distillation of the oily residue
  7. customto remove the low boiling material (50°-60° C./5 mmHg)

Sources & evidence

ORD record
ord-005d6efe11d24c179d57afc70367f3a9
Source dataset
uspto-grants-1986_05
Patent number
US04591458

Reaction notes

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