2,4-Dichlorobenzoyl chloride → 2,4-Dichloro-N-[(8-cyclopropylmethyl-1,4-dioxaspiro[4.5]dec-8-yl)methyl]benzamide

HRID 1865458Notes

Reaction equation

HRID 1865458 reaction equation
[CH:1]1([CH2:4][C:5]2([CH2:15][NH2:16])[CH2:14][CH2:13][C:8]3([O:12][CH2:11][CH2:10][O:9]3)[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.C(N(C(C)C)C(C)C)C.[Cl:26][C:27]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:28]=1[C:29](Cl)=[O:30]>C(Cl)Cl>[Cl:26][C:27]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:28]=1[C:29]([NH:16][CH2:15][C:5]1([CH2:4][CH:1]2[CH2:3][CH2:2]2)[CH2:14][CH2:13][C:8]2([O:12][CH2:11][CH2:10][O:9]2)[CH2:7][CH2:6]1)=[O:30]

Participants

5

Reactant 3

HCID 666452,4-Dichlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 686836208-(Cyclopropylmethyl)-1,4-dioxaspiro[4.5]decane-8-methanamine

Product 1

HCID 686824732,4-Dichloro-N-[(8-cyclopropylmethyl-1,4-dioxaspiro[4.5]dec-8-yl)methyl]benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {[8-(cyclopropylmethyl)-1,4-dioxaspiro[4.5]dec-8-yl]methyl}amine (7 g; 31.0 mmol) and n-ethyldiisopropylamine (6.45 ml; 37.2 mmol) in DCM (60 ml) at 0° C. was added 2,4-dichlorobenzoyl chloride (4.781 ml; 34.17 mmol) dropwise and the solution stirred for 4 hours warming to ambient temperature. The reaction was partitioned between DCM (50 ml) and water (20 ml). The aqueous phase was extracted with DCM (20 ml) and the combined organics dried over MgSO4, filtered and evaporated to give a colourless oil which was used in the next step without further purification. (11.5 g) 1H NMR δ (ppm)(CDCl3): 7.67 (1H, d, J=8.3 Hz), 7.43 (1H, d, J=2.0 Hz), 7.32 (1H, dd, J=2.0, 8.4 Hz), 6.25 (1H, s), 3.93 (4H, s), 3.56 (2H, d, J=6.2 Hz), 1.67 (8H, m)), 1.33 (2H, d, J=6.7 Hz), 0.75-0.65 (1H, m), 0.51-0.47 (2H, m), 0.05 (2H, q, J=5.0 Hz). MS (m/e)=398

Workup

  1. customThe reaction was partitioned between DCM (50 ml) and water (20 ml)
  2. extractionThe aqueous phase was extracted with DCM (20 ml)
  3. dry with materialthe combined organics dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto give a colourless oil which
  7. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-7bedd9be41a641fcb2b5dbbf162aed90
Source dataset
uspto-grants-2009_12
Patent number
US07626056B2

Reaction notes

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