Methyl chloroformate → HCID 21758341, compound

HRID 2379980Notes

Reaction equation

HRID 2379980 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][NH2:17])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.C(N(CC)CC)C.Cl[C:28]([O:30][CH3:31])=[O:29].[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]/[C:35]([OH:37])=[O:36]>C(Cl)Cl.C(O)C>[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]/[C:35]([OH:37])=[O:36].[F:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][NH:17][C:28](=[O:29])[O:30][CH3:31])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 444972Fumaric AcidHCID 146998572-(4-(6-Fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)ethan-1-amine

Product 1

HCID 21758341HCID 21758341, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethylamine (2.0 gm, 7.6 mmol) and triethylamine (1.0 gm, 10 mmol) in DCM (50 ml) was treated with methyl chloroformate (860 mg, 9.12 mmol) dropwise at room temperature. The mixture was stirred for 1 hr. The reaction mixture was diluted with DCM and washed with brine. The organic solution was dried over MgSO4 and concentrated to a crude oil. The purification was done by flash chromatography over a silica gel column (28 gm of Sorbsil C-30, eluted with DCM and MeOH/DCM). The pure oil thus obtained weighed 2.34 gm. It was converted to a fumarate salt by treatment with fumaric acid (840 mg, 1.0 eq) in ethanol. Crystallization was induced by adding drops of isopropyl ether, yield: 2.31 gm, m.p.=163°-165° C.

Workup

  1. washwashed with brine
  2. dry with materialThe organic solution was dried over MgSO4
  3. concentrationconcentrated to a crude oil
  4. customThe purification
  5. washwas done by flash chromatography over a silica gel column (28 gm of Sorbsil C-30, eluted with DCM and MeOH/DCM)
  6. customThe pure oil thus obtained
  7. customCrystallization
  8. additionby adding drops of isopropyl ether, yield: 2.31 gm, m.p.=163°-165° C.

Sources & evidence

ORD record
ord-52b8dd50ff614653a823892e53bff986
Source dataset
uspto-grants-1994_11
Patent number
US05364866

Reaction notes

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