Diisopropylethylamine → HCID 178523333, compound

HRID 1643244Notes

Reaction equation

HRID 1643244 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[C:12]([C@@H:16]2[CH2:21][O:20][C@@H:19]([CH2:22][CH2:23][CH2:24][NH2:25])[O:18][CH2:17]2)=[CH:11][CH:10]=[CH:9]3)[CH2:3][CH2:2]1.Cl[C:27]([O:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)=[O:28].C(N(CC)C(C)C)(C)C>ClCCl>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[C:12]([C@@H:16]2[CH2:21][O:20][C@@H:19]([CH2:22][CH2:23][CH2:24][NH:25][C:27](=[O:28])[O:29][C:30]4[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=4)[O:18][CH2:17]2)=[CH:11][CH:10]=[CH:9]3)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1390594-Chlorophenyl chloroformateHCID 178511032HCID 178511032, compound

Product 1

HCID 178523333HCID 178523333, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.205 g (0.60 mmol) of trans-3-[5-(6-cylcopropylmethoxynaphthalen-1-yl)-1,3-dioxan-2-yl]propylamine is added, in small portions and at ambient temperature, to a solution of 0.110 ml (0.78 mmol) of 4-chlorophenyl chloroformate and 0.205 ml (1.2 mmol) of N,N-diisopropylethylamine in 6 ml of dichloromethane. The mixture is stirred at ambient temperature for 16 hours, then washing is carried out with 5 ml of a saturated sodium bicarbonate solution. The phases are separated and the organic phase is filtered through a hydrophobic sintered glass funnel. The filtrate is concentrated under reduced pressure and the residue is purified by chromatography on silica gel, eluting with an 80/20 mixture of cyclohexane and ethyl acetate. After washing in 5 ml of diisopropyl ether, 0.176 g of a white solid is obtained.

Workup

  1. washwashing
  2. customThe phases are separated
  3. filtrationthe organic phase is filtered through a hydrophobic sintered glass funnel
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. customthe residue is purified by chromatography on silica gel
  6. washeluting with an 80/20 mixture of cyclohexane and ethyl acetate
  7. washAfter washing in 5 ml of diisopropyl ether

Sources & evidence

ORD record
ord-9edb859437964750a04112bb9e461e33
Source dataset
uspto-grants-2012_02
Patent number
US08119687B2

Reaction notes

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