4-Methylmorpholine → HCID 69433369, compound

HRID 1376051Notes

Reaction equation

HRID 1376051 reaction equation
[CH2:1]([N:3]([CH2:19][CH3:20])[CH2:4][CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])[N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)[CH3:2].[NH:21]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C@@H:22]([C:31](O)=[O:32])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>C(Cl)Cl>[C:37]([O:36][C:34](=[O:35])[NH:21][CH:22]([CH2:23][C:24]1[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=1)[C:31]([N:9]1[CH2:8][CH2:7][N:6]([CH:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[CH2:4][N:3]([CH2:1][CH3:2])[CH2:19][CH3:20])[CH2:11][CH2:10]1)=[O:32])([CH3:40])([CH3:38])[CH3:39]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 7018791N-Boc-4-chloro-D-phenylalanineHCID 58786461HCID 58786461, compound

Product 1

HCID 69433369HCID 69433369, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To Diethyl-[2-(2-fluoro-phenyl)-2-piperazin-1-yl-ethyl]-amine (513) (0.206 g, 0.738 mmol) was added Boc-4-chloro-D-Phe (0.221 g, 0.738 mmol), 1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.141 g, 0.738 mmol), 1-Hydroxybenzotriazole hydrate (0.099 g, 0.738 mmol), DCM (5.0 mL) and 4-methylmorpholine (0.243 mL, 2.215 mmol). The reaction was allowed to stir at room temperature for 4 h. The reaction mixture was concentrated to dryness. The resulting residue was taken up in EtOAc (30 mL) and washed with sat. NaHCO3 and brine. The crude material was purified by chromatography (silica gel 60 mesh, eluting with 5% MeOH/5% TEA in EtOAc) yielding 0.41 g (99%) pure product.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. washwashed with sat. NaHCO3 and brine
  3. customThe crude material was purified by chromatography (silica gel 60 mesh, eluting with 5% MeOH/5% TEA in EtOAc)

Sources & evidence

ORD record
ord-d2c841fe928f4989b0911752f1b5b8f6
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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