Trifluoroacetic acid → HCID 9839506, compound

HRID 343920Notes

Reaction equation

HRID 343920 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[CH2:5][C@@H:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][C@@H:7]1[NH2:15].[CH3:20]CCCCC.C(O)C.C(O)(C(F)(F)F)=O>O.C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[CH2:5][C@@H:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][C@@H:7]1[NH:15][CH3:20]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 21879635Ethanol hexaneHCID 22941677HCID 22941677, compound

Product 1

HCID 9839506HCID 9839506, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

(±)cis-1-(3,4-Dichlorobenzyl)-2-methylaminoindane (7.49 g) was prepared from (±)cis-1-(3,4-dichlorobenzyl)-2-aminoindane (Preparation 2, Method B, 13.95 g) as described in Preparations 3-5 , and then converted into the single enantiomers (+)cis-1-(3,4-dichlorobenzyl)-2-methylaminoindane hydrochloride(E1) and (-)cis-1-(3,4-dichlorobenzyl)-2-methylaminoindane hydrochloride(E2) as described above. In each case chiral purity was greater than 99.5% as judged by chiral HPLC analysis (Column: CHIRALPAK AD; Eluent: 99/1 hexane/ethanol+0.1% DEA). The level of other impurities was<0.3% as judged by HPLC (Column: Merck RP--Select B. Eluent A: 0.1% TFA in water; Eluent B 0.1% TFA in acetonitrile; Eluent composition increased linearly from 5%B to 80% B over 40min. and then held at 80% B for a further 10 min).

Workup

  1. temperatureEluent composition increased linearly from 5%B to 80% B over 40min.

Sources & evidence

ORD record
ord-5992d04136f4450ea4a56dec569a329c
Source dataset
uspto-grants-1999_01
Patent number
US05863952

Reaction notes

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