Trifluoroacetic acid → HCID 9843118, compound

HRID 1057617Notes

Reaction equation

HRID 1057617 reaction equation
[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]3)[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:22][CH2:23][N:24]3[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]3)[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 12967333HCID 12967333, compound

Product 1

HCID 9843118HCID 9843118, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-Butyl 4-{2-[(9-Benzyl-9H-carbazol-4-yl)oxy]ethyl}-1-piperazinecarboxylate (0.0450 g, 0.0927 mmol), trifluoroacetic acid (2.5 mL), and CH2Cl2 (2.5 mL) is stirred at room temperature for 1 h. Trifluoroacetic acid and CH2Cl2 are then removed in vacuo and the residue is partitioned between CH2Cl2 and aq. sodium bicarbonate. The organic layers are dried over sodium sulfate and taken to dryness to give 0.0326 g (91%) of the title compound; IR (drift) 2935, 2821, 1584, 1456, 1353, 1342, 1332, 1271, 1245, 1154, 1145, 1112, 783, 750, 715 cm−1; 1H NMR (CDCl3) δ2.70, 2.95, 3.04, 4.41, 5.50, 6.69, 6.99, 7.12, 7.2-7.4, 8.39. Anal. Calcd for C25H27N3O: C, 77.89; H, 7.06; N, 10.90. Found: C, 76.35; H, 7.20; N, 10.30.

Workup

  1. customTrifluoroacetic acid and CH2Cl2 are then removed in vacuo
  2. customthe residue is partitioned between CH2Cl2 and aq. sodium bicarbonate
  3. dry with materialThe organic layers are dried over sodium sulfate

Sources & evidence

ORD record
ord-03f09a08098d488f8b0c80a296844b0f
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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