Acetyl chloride → HCID 42645070, compound

HRID 1809061Notes

Reaction equation

HRID 1809061 reaction equation
C[C:2]1([CH3:22])[CH2:8][CH2:7][CH2:6][N:5]([C:9]([C:11]2[CH:15]=[C:14]([CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[S:13][CH:12]=2)=[O:10])[CH2:4][CH2:3]1.[C:23](Cl)(=[O:25])[CH3:24].[CH2:27]([N:29](CC)CC)C>C(Cl)Cl>[CH2:6]1[N:5]([C:9]([C:11]2[CH:15]=[C:14]([CH:16]3[CH2:17][CH2:18][N:19]([C:23](=[O:25])[CH3:24])[CH2:20][CH2:21]3)[S:13][CH:12]=2)=[O:10])[CH2:4][CH2:3][N:29]2[CH2:27][CH2:22][CH2:2][CH2:8][CH:7]12

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 59542473HCID 59542473, compound

Product 1

HCID 42645070HCID 42645070, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4,4-Dimethyl-azepan-1-yl)-(5-piperidin-4-yl-thiophen-3-yl)-methanone (0.02 g) was dissolved in DCM (2 mL) and triethylamine (0.1 mL). Acetyl chloride (0.1 mL) was added and the mixture stirred for 1 hour. The organic solution was washed with 1 N hydrochloric acid, dried over anhydrous magnesium sulphate, filtered and evaporated to give a colourless oil. The oil was purified by flash chromatography on silica eluting with 10% methanol in ethyl acetate. The fractions containing the desired product were concentrated under vacuum to give the title compound (38 mg) as a clear oil. LCMS m/z 363.13 [M+H]+RT=9.40 min (Analytical Method 2). 1H NMR (400 MHz, CHCl3-d): δ 7.3 (s, 1H), 6.9 (s, 1H), 4.4 (m, 1H), 3.9 (m, 1H), 3.7-3.4 (m, 4H), 3.2 (m, 1H), 3.0 (m, 1H), 2.6 (m, 1H), 2.15 (s, 3H), 2.1-2.0 (m, 2H), 1.8-1.4 (m, 9H), 1.0 (s, 3H), 0.9 (s, 3H).

Workup

  1. washThe organic solution was washed with 1 N hydrochloric acid
  2. dry with materialdried over anhydrous magnesium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customto give a colourless oil
  6. customThe oil was purified by flash chromatography on silica eluting with 10% methanol in ethyl acetate
  7. additionThe fractions containing the desired product
  8. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-e00041238853497288a689f78fe4319d
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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