Water → 1-{4-[4-(2-Phenylethyl)-1,3-thiazol-2-yl]piperidin-1-yl}pentan-1-one

HRID 549950Notes

Reaction equation

HRID 549950 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].Cl.[C:9]1([CH2:15][CH2:16][C:17]2[N:18]=[C:19]([CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[S:20][CH:21]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C.O>ClCCl>[C:9]1([CH2:15][CH2:16][C:17]2[N:18]=[C:19]([CH:22]3[CH2:27][CH2:26][N:25]([C:1](=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5])[CH2:24][CH2:23]3)[S:20][CH:21]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 671568834-[4-(2-Phenylethyl)-1,3-thiazol-2-yl]piperidine hydrochloride

Product 1

HCID 671568721-{4-[4-(2-Phenylethyl)-1,3-thiazol-2-yl]piperidin-1-yl}pentan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pentanoyl chloride (133 mg) is added to a solution of 4-[4-(2-phenylethyl)-1,3-thiazol-2-yl]piperidine hydrochloride (II-1, 309 mg) and triethylamine (0.7 ml) in dichloromethane (3 ml). The mixture is stirred overnight, and water is then added. The aqueous phase is separated off and extracted with ethyl acetate, and the combined organic phases are then dried with sodium sulphate and concentrated. The residue is purified. This gives 1-{4-[4-(2-phenylethyl)-1,3-thiazol-2-yl]piperidin-1-yl}pentan-1-one (179 mg).

Workup

  1. customThe aqueous phase is separated off
  2. extractionextracted with ethyl acetate
  3. dry with materialthe combined organic phases are then dried with sodium sulphate
  4. concentrationconcentrated
  5. customThe residue is purified

Sources & evidence

ORD record
ord-d97bd6efa9634581932a90683c79308f
Source dataset
uspto-grants-2011_05
Patent number
US07943774B2

Reaction notes

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