4-(4-Chlorophenyl)-4-hydroxypiperidine → HCID 12043490, compound

HRID 2184929Notes

Reaction equation

HRID 2184929 reaction equation
C(OC(=O)N)(C)(C)C.ClC1C=CC(C2(O)CCNCC2)=CC=1.C(OC(=O)[NH:29][CH:30]1[CH:35]2[CH:31]1[CH2:32][N:33]([CH2:36][C:37](=[O:54])[NH:38][C:39]1[CH:40]=[CH:41][C:42]3[N:43]([CH2:52][CH3:53])[C:44]4[C:49]([C:50]=3[CH:51]=1)=[CH:48][CH:47]=[CH:46][CH:45]=4)[CH2:34]2)(C)(C)C.Cl.O1CCOCC1>>[CH2:52]([N:43]1[C:42]2[CH:41]=[CH:40][C:39]([NH:38][C:37](=[O:54])[CH2:36][N:33]3[CH2:32][CH:31]4[CH:35]([CH:30]4[NH2:29])[CH2:34]3)=[CH:51][C:50]=2[C:49]2[C:44]1=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH3:53]

Participants

5

Reactant 4

HCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 77922tert-Butyl carbamate2×HCID 204431481,4-Dioxane hydrochlorideHCID 70173098HCID 70173098, compound

Product 1

HCID 12043490HCID 12043490, compound

Procedure

3-[(9-Ethyl-9H-carbazol-3-ylcarbamoyl)-methyl]-3-aza-bicyclo[3.1.0]hex-6-yl}-carbamic acid tert-butyl ester was synthesized similarly to example 44, substituting 3-aza-bicyclo[3.1.0]hex-6-yl)-carbamic acid tert-butyl ester for 4-(4-Chlorophenyl)-4-hydroxypiperidine and substituting the compound of example 19 for the compound of example 40. A solution of {3-[(9-ethyl-9H-carbazol-3-ylcarbamoyl)-methyl]-3-aza-bicyclo[3.1.0]hex-6-yl}-carbamic acid tert-butyl ester (4.6 mmol) in 1:1 4 M HCl/dioxane (25 mL) was stirred at room temperature for 16 hours. The reaction mixture was then concentrated, and the residue was concentrated from diethyl ether (2×25 mL). The pale yellow foam remaining (723 mg, 37%) was N-(9-ethyl-9H-carbazol-3-yl)-2-(6-amino-3-aza-bicyclo[3.1.0]hex-3-yl)-acetamide.

Workup

  1. customwas synthesized similarly to example 44
  2. concentrationThe reaction mixture was then concentrated
  3. concentrationthe residue was concentrated from diethyl ether (2×25 mL)

Sources & evidence

ORD record
ord-4991b74ae6df45f3b751b0cbb09a4dbf
Source dataset
uspto-grants-2002_06
Patent number
US06399631B1

Reaction notes

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