Trifluoroacetic acid → (1,4-Diazepan-1-yl)(tetrahydro-2H-pyran-4-yl)methanone

HRID 1920721Notes

Reaction equation

HRID 1920721 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[O:16])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[N:11]1([C:15]([CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[O:16])[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 591433904-(Tetrahydro-pyran-4-carbonyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 28776660(1,4-Diazepan-1-yl)(tetrahydro-2H-pyran-4-yl)methanoneYield 258.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 13 g (41.7 mmol) of 4-(tetrahydro-pyran-4-carbonyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester in DCM (260 mL) were added 32.5 mL of trifluoroacetic acid. The reaction was stirred for 6 h at room temperature. The solvent was removed under reduced pressure. The residual oil was azeotroped with DCM (3×20 mL), chloroform (2×20 mL) and toluene (3×20 mL) to afford 22.9 g of [1,4]diazepan-1-yl-(tetrahydro-pyran-4-yl)-methanone as triple trifluoroacetic acid salt; ES−MS: m/z 213 [M+H+]

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residual oil was azeotroped with DCM (3×20 mL), chloroform (2×20 mL) and toluene (3×20 mL)

Sources & evidence

ORD record
ord-dda95f6b1324459381c6d5ea2c50a92b
Source dataset
uspto-grants-2012_05
Patent number
US08173638B2

Reaction notes

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