4-Methylmorpholine → HCID 70158247, compound

HRID 2301760Notes

Reaction equation

HRID 2301760 reaction equation
Cl.[CH3:2][NH:3][CH:4]1[CH2:8][CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]([CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([N:22]([C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])[CH2:23][CH2:24][CH3:25])[CH2:18][CH2:17]2)[CH2:5]1.CN1CCOCC1.[Cl:43][C:44]1[CH:52]=[CH:51][CH:50]=[CH:49][C:45]=1[C:46](Cl)=[O:47]>C(Cl)Cl>[ClH:43].[CH3:2][N:3]([CH:4]1[CH2:8][CH:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:6]([CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([N:22]([C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])[CH2:23][CH2:24][CH3:25])[CH2:18][CH2:17]2)[CH2:5]1)[C:46]([C:45]1[CH:49]=[CH:50][CH:51]=[CH:52][C:44]=1[Cl:43])=[O:47]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 691102-Chlorobenzoyl chlorideHCID 70158564HCID 70158564, compound

Product 1

HCID 70158247HCID 70158247, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(RS)-(methylamino)-3-(SR)-((4-(N-(benzyloxycarbonyl)-N-(propyl)amino)piperidin-1-yl)methyl)-4-(SR)-phenylcyclopentane hydrochloride from Step A (5.5 mg, 0.012 mmol) in methylene chloride (1 mL) was added N-methyl morpholine (0.005 mL, 0.035 mmol) and 2-chlorobenzoyl chloride (4 mg, 0.024 mmol). After 16 h, the reaction was concentrated and the residue purified on Prep TLC to afford the free amine of the title compound. This was taken up in ether and excess 1N hydrogen chloride in ether was added. The volatiles were removed under a stream of nitrogen and evaporated to dryness under vacuum.

Workup

  1. concentrationthe reaction was concentrated
  2. customthe residue purified on Prep TLC

Sources & evidence

ORD record
ord-e1485e20b6254358924dd705188014b5
Source dataset
uspto-grants-2002_12
Patent number
US06500844B1

Reaction notes

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