Acetyl chloride → HCID 89501634, compound

HRID 874741Notes

Reaction equation

HRID 874741 reaction equation
[C:1](Cl)([CH3:3])=[O:2].CCN(CC)CC.Cl.[CH:13]1([CH:18]([NH2:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1>C(Cl)Cl>[CH:13]1([CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[NH:25][C:1](=[O:2])[CH3:3])[CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86263098HCID 86263098, compound

Product 1

HCID 89501634HCID 89501634, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

AcCl (0.10 g, 1.25 mmol) was added to a stirred suspension of Et3N (0.35 mL, 0.25 g, 2.5 mmol, 2.2 eq.) and (rac)-1-cyclopentyl-1-(2-pyridinyl)methylamine HCl salt (0.25 g, 1.14 mmol) in CH2Cl2 (5 mL). The resulting mixture was stirred at rt for 2 h. The reaction mixture was washed with H2O (10%, 3×3 mL) and was dried over Na2SO4 and was concentrated under reduced pressure yielding the crude product (0.20 g) as a clear yellow oil which quickly crystallized. 1H NMR (300 MHz, CDCl3) δ ppm 8.53 (d, J=5.0 Hz, 1H), 7.62 (dt, J=1.5, 7.5 Hz, 1H), 7.28 (t, J=7.5 Hz, 1H), 7.16 (d, J=5.0 Hz, 1H), 6.72 (br d, J=7.0 Hz, 1H), 4.93 (t, J=9.0 Hz, 1H), 2.37-2.20 (m, 1H), 2.00 (s, 3H), 1.80-1.10 (m, 8H); HPLC: Daicel Chiralpak AD-H, 80:20 v/v heptane-EtOH (+0.2% Et2NH), 1.0 mL min−1, 210 nm, Rt=9.5 min, Rt=19.2 min.

Workup

  1. washThe reaction mixture was washed with H2O (10%, 3×3 mL)
  2. dry with materialwas dried over Na2SO4
  3. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-4f4185e942854083b009babe3fb8e719
Source dataset
uspto-grants-2015_03
Patent number
US08980934B2

Reaction notes

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