Trifluoroacetic acid → 3-(3-(4-Chlorobenzyl)azetidin-1-yl)propan-1-amine

HRID 1182100Notes

Reaction equation

HRID 1182100 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:14][CH:13]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH2:12]1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][CH:13]2[CH2:14][N:11]([CH2:10][CH2:9][CH2:8][NH2:7])[CH2:12]2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69411053{3-[3-(4-Chloro-benzyl)-azetidin-1-yl]-propyl}carbamic acid tert-butyl ester

Product 1

HCID 694091233-(3-(4-Chlorobenzyl)azetidin-1-yl)propan-1-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {3-[3-(4-chloro-benzyl)-azetidin-1-yl]-propyl}-carbamic acid tert-butyl ester (0.48 g, 1.43 mmol) in DCM (5 ml) is treated with trifluoroacetic acid (2 ml) and the reaction mixture stirred for 1.25 hours. The solvent is evaporated and the crude product partitioned between 1 M sodium hydroxide solution and 20% isopropanol in DCM. The organic phase is evaporated to afford 3-[3-(4-chloro-benzyl)-azetidin-1-yl]-propylamine. [M+H] 239.13.

Workup

  1. customThe solvent is evaporated
  2. customthe crude product partitioned between 1 M sodium hydroxide solution and 20% isopropanol in DCM
  3. customThe organic phase is evaporated

Sources & evidence

ORD record
ord-30d854ffd4d44fbcabb1be1be1dc836c
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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