Pyridine → Benzyl N-(4-hydroxybutyl)carbamate

HRID 514597Notes

Reaction equation

HRID 514597 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6].N1C=CC=CC=1.[CH2:13]([O:20][C:21](Cl)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>ClCCl>[OH:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:21](=[O:22])[O:20][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 258684-Amino-1-butanol

Product 1

HCID 3366758Benzyl N-(4-hydroxybutyl)carbamateYield 27.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-amino-1-butanol (7.68 g) and pyridine (7.00 g) in dichloromethane (100 mL) was chilled in an ice bath and a solution of benzylchloroformate (14.37 g) in dichloromethane (100 mL) was slowly added with stirring over a period of thirty minutes. The ice bath was removed and the reaction was stirred for an additional 16 hours. Hydrochloric acid (1.2 M, 200 mL) was added and phases were separated. The organic phase was dried (MgSO4), filtered and concentrated under reduced pressure. The resulting residue was recrystallized from toluene and dried under vacuum to provide 5.15 g of benzyl (4-hydroxybutyl)carbamate.

Workup

  1. customThe ice bath was removed
  2. stirringthe reaction was stirred for an additional 16 hours
  3. additionHydrochloric acid (1.2 M, 200 mL) was added
  4. customphases were separated
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was recrystallized from toluene
  9. customdried under vacuum

Sources & evidence

ORD record
ord-9eb057dddaf64ecaaa387cad8408942b
Source dataset
uspto-grants-2015_08
Patent number
US09107958B2

Reaction notes

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