Trifluoroacetic acid → 1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]-4-phenylpiperidin-4-amine

HRID 715610Notes

Reaction equation

HRID 715610 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=2)[C:10]2[C:15]([N:16]=1)=[C:14]([N:17]1[CH2:22][CH2:21][C:20]([NH:29]C(=O)OC(C)(C)C)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:19][CH2:18]1)[N:13]=[CH:12][N:11]=2.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:37]2[CH:38]=[CH:39][C:40]([Cl:43])=[CH:41][CH:42]=2)[C:10]2[C:15]([N:16]=1)=[C:14]([N:17]1[CH2:22][CH2:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)([NH2:29])[CH2:19][CH2:18]1)[N:13]=[CH:12][N:11]=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71455552tert-butyl N-{1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]-4-phenylpiperidin-4-yl}carbamate

Product 1

HCID 714501881-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]-4-phenylpiperidin-4-amineYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl N-{1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]-4-phenylpiperidin-4-yl}carbamate (2.65 g, 4.3 mmol) was stirred in dichloromethane (32 mL) and trifluoroacetic acid (8 mL) for 1.5 h. The reaction was concentrated in vacuo. The crude product was dissolved in ethyl acetate and washed with 3.8 M NaOH. The aqueous layer was extracted twice with ethyl acetate. The combined organic layer was washed with brine and dried with MgSO4 to yield 2.21 g (99%) of pure 1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]-4-phenylpiperidin-4-amine. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.87 (d, J=13.56 Hz, 2 H) 2.15-2.39 (m, 2 H) 3.82-4.11 (m, 2 H) 5.10 (br. s., 2 H) 7.11-7.62 (m, 13 H) 8.40 (s, 1 H), [M+H]+ 515.8.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionThe crude product was dissolved in ethyl acetate
  3. washwashed with 3.8 M NaOH
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried with MgSO4

Sources & evidence

ORD record
ord-9222c858b8ab4c8385391344229777f0
Source dataset
uspto-grants-2015_11
Patent number
US09187480B2

Reaction notes

Loading…