Trifluoroacetic acid → 1-[4-(3-Piperidin-1-yl-propoxy)-benzyl]-[1,4]diazepane

HRID 1434567Notes

Reaction equation

HRID 1434567 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[N:26]1([CH2:25][CH2:24][CH2:23][O:22][C:19]2[CH:20]=[CH:21][C:16]([CH2:15][N:11]3[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]3)=[CH:17][CH:18]=2)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 102964254-[4-(3-Piperidin-1-yl-propoxy)-benzyl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 596405921-[4-(3-Piperidin-1-yl-propoxy)-benzyl]-[1,4]diazepaneYield 89.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[4-(3-Piperidin-1-yl-propoxy)-benzyl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester (D3) (2.27 g, 5.27 mmol) was dissolved in dichloromethane (10 ml), treated with trifluoroacetic acid (5 ml) and stirred at room temperature under argon for 2 hours. The solvent was removed in vacuo and the residue dissolved in methanol and passed down an SCX column (10 g) eluting with methanol followed by 0.88 ammonia/methanol (1:9). The basic fractions were combined and concentrated in vacuo to afford the title compound (1.57 g).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in methanol
  3. washeluting with methanol
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-143a97be32394813984dc4f3a46bc604
Source dataset
uspto-grants-2009_11
Patent number
US07615550B2

Reaction notes

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