Hydrochloric Acid → tert-Butyl (2-((4-chlorobenzyl)amino)ethyl)carbamate

HRID 1192330Notes

Reaction equation

HRID 1192330 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].Cl>ClCCCl>[C:7]([O:6][C:5](=[O:11])[NH:4][CH2:3][CH2:2][NH:1][CH2:17][C:16]1[CH:19]=[CH:20][C:13]([Cl:12])=[CH:14][CH:15]=1)([CH3:8])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 77264-ChlorobenzaldehydeHCID 187201N-BOC-ethylenediamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 67134877tert-Butyl (2-((4-chlorobenzyl)amino)ethyl)carbamateYield 56.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of tert-butyl N-(2-aminoethyl)carbamate (1.00 g, 6.24 mmol) and 4-chlorobenzaldehyde (0.90 g, 6.37 mmol) in DCE (10 mL) was stirred for 30 minutes, followed by the addition of NaBH(OAc)3 (1.98 g, 9.36 mmol) in a single portion. After being stirred for 12 hours, the mixture was acidified to pH 2 with 0.2N HCl, and extracted with DCM (3 times, each discarded). The acidic aqueous layer was basified to pH 10 with 2.0 M NaOH, and extracted with DCM. The DCM extracts were dried (Na2SO4), filtered, and concentrated in vacuo to give [2-(4-chlorobenzylamino)-ethyl]-carbamic acid tert-butyl ester as an oil (1.0 g). LCMS (APCI+) m/z 285, 287 [M+H]+.

Workup

  1. extractionextracted with DCM (3 times
  2. extractionextracted with DCM
  3. dry with materialThe DCM extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-464fae773f9a4bf6b8e06cbdae316ec7
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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