(S)-1-(4-Fluorophenyl)-ethylamine → HCID 86629623, compound

HRID 911381Notes

Reaction equation

HRID 911381 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1OS(C(F)(F)F)(=O)=O.[F:27][C:28]1[CH:33]=[CH:32][C:31]([C@@H:34]([NH2:36])[CH3:35])=[CH:30][CH:29]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:14])([F:15])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1[NH:36][C@H:34]([C:31]1[CH:32]=[CH:33][C:28]([F:27])=[CH:29][CH:30]=1)[CH3:35]

Participants

4

Reactant 2

HCID 2779063(S)-1-(4-Fluorophenyl)-ethylamineHCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 86629623HCID 86629623, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Use a method similar to the General Procedure 5-2 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (7.0 g, 16.4 mmol) with (S)-1-(4-fluorophenyl)ethylamine (6.9 g, 49.3 mmol) in toluene (175 mL). Purify by chromatography on silica gel eluting with hexane/EtOAc (9:1 to 1:1) followed by SCX chromatography [pre-wash column with methanol followed by DCM, load material dissolved in DCM, then elute with DCM/2M ammonia in methanol (1:1) and concentrate in vacuo] to give 7-chloro-6-[1-(S)-(4-fluorophenyl)-ethylamino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (3.96 g, 58%). GC-MS m/z: 414 (M+).

Workup

  1. customPurify by chromatography on silica gel eluting with hexane/EtOAc (9:1 to 1:1)
  2. washpre-wash column with methanol
  3. dissolutiondissolved in DCM
  4. washelute with DCM/2M ammonia in methanol (1:1)
  5. concentrationconcentrate in vacuo]

Sources & evidence

ORD record
ord-245cea2387694fedb023d3f363a380ae
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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