Diisopropylethylamine → HCID 18735046, compound

HRID 844488Notes

Reaction equation

HRID 844488 reaction equation
[ClH:1].Cl.CO[C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]([CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[CH:10]([NH2:22])[CH2:9][CH2:8]2.[C:23]([C:26]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:31][CH2:30][N:29]([CH2:32][C:33]([OH:35])=O)[CH2:28][CH2:27]1)(=[O:25])[CH3:24].C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O>[ClH:1].[ClH:1].[C:23]([C:26]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:27][CH2:28][N:29]([CH2:32][C:33]([NH:22][C@H:10]2[CH2:9][CH2:8][C:7]3[C:12](=[CH:13][CH:14]=[CH:5][CH:6]=3)[C@H:11]2[CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[O:35])[CH2:30][CH2:31]1)(=[O:25])[CH3:24]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22037061HCID 22037061, compoundHCID 22037065HCID 22037065, compound

Product 1

HCID 18735046HCID 18735046, compoundYield 179.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,2,3,4-Tetrahydro-1-(3-pyridinylmethyl)-2-naphthalenamine bis-hydrochloride 4 (0.75 g, 2.41 mmol) was reacted with 2-(4-acetyl-4-phenyl-piperidin-1-yl)acetic acid (0.86 g, 2.65 mmol), N,N-diisopropylethylamine (2.0 mL, 11.3 mmol) and HBTU (1.01 g, 2.65 mmol) in N,N-dimethylformamide (15 mL) at room temperature for 2 h as described above in EXAMPLES 7-8. The product was collected by filtration from the aqueous work-up. This material was dissolved in isopropanol (˜30 mL) and treated with a saturated solution of hydrochloric acid in isopropanol (˜5 mL). The solvent was evaporated in vacuo, and the residue was triturated with diethyl ether to give 4-acetyl-4-phenyl-N-[cis-1,2,3,4-tetrahydro-1-(3-pyridinylmethyl)-2-naphthalenyl]-1-piperidineacetamide bis-hydrochloride 21 as an amorphous pale yellow solid (1.2 g, 90%): MS m/e 482 (MH+) (Scheme 34).

Workup

  1. filtrationThe product was collected by filtration from the aqueous work-up
  2. dissolutionThis material was dissolved in isopropanol (˜30 mL)
  3. additiontreated with a saturated solution of hydrochloric acid in isopropanol (˜5 mL)
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-26f870adfb5641ec858b1768aca56c36
Source dataset
uspto-grants-2002_04
Patent number
US06380224B1

Reaction notes

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