Triethylamine → N-Cbz-N,N-bis(2-chloroethyl)amine

HRID 1966110Notes

Reaction equation

HRID 1966110 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].Cl.[Cl:13][CH2:14][CH2:15][NH2:16].[Cl:17][CH2:18][CH2:19]N.C(N(CC)CC)C>ClCCl.O1CCCC1>[Cl:13][CH2:14][CH2:15][N:16]([CH2:19][CH2:18][Cl:17])[C:2](=[O:3])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 86583559Bis(2-chloroethylamine) hydrochloride

Product 1

HCID 12553191N-Cbz-N,N-bis(2-chloroethyl)amineYield 26%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

13.2 ml (92 mmol) of benzyl chloroformate are added slowly to a solution, cooled to 0° C., of 15 g (84 mmol) of bis(2-chloroethylamine) hydrochloride, 26 ml (185 mmol) of triethylamine in 200 ml of dichloromethane and 70 ml of tetrahydrofuran, stirred beforehand for 15 min and then filtered in order to remove the triethylammonium chloride. The reaction medium is stirred at ambient temperature for 18 h. After the addition of water, the reaction medium is extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and evaporated. 20 g of crude residue are obtained and purified by chromatography on silica gel, elution being carried out with an 8/2 heptane/ethyl acetate mixture. 6 g (26%) of benzyl bis(2-chloroethyl)carbamate are thus obtained.

Workup

  1. filtrationfiltered in order
  2. customto remove the triethylammonium chloride
  3. stirringThe reaction medium is stirred at ambient temperature for 18 h
  4. additionAfter the addition of water
  5. extractionthe reaction medium is extracted with ethyl acetate
  6. dry with materialThe organic phase is dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. custom20 g of crude residue are obtained
  10. custompurified by chromatography on silica gel, elution

Sources & evidence

ORD record
ord-8f5e9c7694cd4be0b5379c394c6db49c
Source dataset
uspto-grants-2013_04
Patent number
US08420632B2

Reaction notes

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