Trifluoroacetic acid → HCID 178511030, compound

HRID 1257712Notes

Reaction equation

HRID 1257712 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][C:16]#[N:17])[CH2:10][CH2:9]1)(C)(C)C.[F:19][C:20]([F:25])([F:24])[C:21]([OH:23])=[O:22]>C(Cl)Cl>[F:19][C:20]([F:25])([F:24])[C:21]([OH:23])=[O:22].[NH2:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][C:16]#[N:17])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178453884HCID 178453884, compound

Product 1

HCID 178511030HCID 178511030, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of trans [4-(2-cyano-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester (2.68 g, 10.6 mmol) in DCM (30 mL) was treated with trifluoroacetic acid (30 mL) and the mixture was stirred at ambient temperature for 30 mins then concentrated under vacuum. The residue was azeotroped with toluene (×3) and the resulting oil was triturated (diethyl ether) to give a solid, that was washed with ether and dried to give 2.75 g (97%) of trans 3-(4-amino-cyclohexyl)-propionitrile trifluoroacetic acid salt as a white solid. 1H NMR (400 MHz, CDCl3) δ: 7.88 (br s, 3H), 3.01 (m, 1H), 2.37 (t, 2H), 2.08 (m, 2H), 1.89 (m, 2H), 1.59 (q, 2H), 1.49-1.35 (m, 3H), 1.04 (m, 2H).

Workup

  1. concentrationthen concentrated under vacuum
  2. customThe residue was azeotroped with toluene (×3)
  3. customthe resulting oil was triturated (diethyl ether)
  4. customto give a solid, that
  5. washwas washed with ether
  6. customdried

Sources & evidence

ORD record
ord-3fda497468904d509030f0958a59ecb5
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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