Triethylamine → HCID 86757041, compound

HRID 1068663Notes

Reaction equation

HRID 1068663 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6](Cl)=[O:7].C(N(CC)CC)C.[Cl:25][C:26]1[CH:27]=[C:28]([CH2:33][C@H:34]2[CH2:39][C@H:38]([N:40]3[CH2:45][CH2:44][CH:43]([CH:46]4[C:52]5[CH:53]=[CH:54][CH:55]=[CH:56][C:51]=5[CH2:50][CH2:49][N:48]5[C:57]6[CH:63]=[CH:62][CH:61]=[CH:60][C:58]=6[N:59]=[C:47]45)[CH2:42][CH2:41]3)[CH2:37][CH2:36][NH:35]2)[CH:29]=[CH:30][C:31]=1[Cl:32]>C(Cl)Cl>[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6]([N:35]1[CH2:36][CH2:37][C@@H:38]([N:40]2[CH2:41][CH2:42][CH:43]([CH:46]3[C:52]4[CH:53]=[CH:54][CH:55]=[CH:56][C:51]=4[CH2:50][CH2:49][N:48]4[C:57]5[CH:63]=[CH:62][CH:61]=[CH:60][C:58]=5[N:59]=[C:47]34)[CH2:44][CH2:45]2)[CH2:39][C@@H:34]1[CH2:33][C:28]1[CH:29]=[CH:30][C:31]([Cl:32])=[C:26]([Cl:25])[CH:27]=1)=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 86757042HCID 86757042, compound

Product 1

HCID 86757041HCID 86757041, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,5-di(trifluoromethyl)benzoyl chloride (0.003 mol) and then triethylamine (0.0045 mol) were added dropwise to a mixture of (±)-trans-6-[1-[2-[(3,4-dichlorophenyl)-methyl]-4-piperidinyl]-4-piperidinyl]-11,12-dihydro-6H-benzimidazo[2,1-b][3]benzazepine (0.003 mol) in CH2Cl2 (25ml). The mixture was stirred at RT overnight, washed with water and separated into its layers. The organic layer was dried, filtered and the solvent was evaporated. The residue was purified over silica gel on a glass filter (eluent: CH2Cl2/CH3OH 98/2 to 96/4). The pure fractions were collected and the solvent was evaporated. The residue was dried, yielding 1.23 g (51%) of (±)-trans-1-[3,5-bis(trifluoromethyl)benzoyl]-2-[(3,4-dichlorophenyl)methyl]-4-[4-(11,12-dihydro-6H-benzimidazo[2,1-b][3]benzazepin-6-yl)-1-piperidinyl]piperidine (comp. 63).

Workup

  1. washwashed with water
  2. customseparated into its layers
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was purified over silica gel on a glass
  7. filtrationfilter (eluent: CH2Cl2/CH3OH 98/2 to 96/4)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated
  10. customThe residue was dried

Sources & evidence

ORD record
ord-22c187e8e3c44b1aa803cfc49c5413ef
Source dataset
uspto-grants-2001_06
Patent number
US06251894B1

Reaction notes

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