Thionyl Chloride → 1-(chloromethyl)-1-(cyclohexylamino)cyclopentane HCl salt

HRID 276265

Reaction equation

[CH:1]1([NH:7][C:8]2([CH2:13]O)[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O=S(Cl)[Cl:17]>Cl>[ClH:17].[Cl:17][CH2:13][C:8]1([NH:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

Conditions

Temperature: 70 °C

Procedure

A 4M HCl solution (p-dioxane, 40 mL) containing 1-(cyclohexylamino)-1-(hydroxymethyl)cyclopentane (Method B4a; 1.9 g, 9.6 mmol) and SOCl2 (0.84 mL, 11.5 mmol) was heated to 70° C. for 18 h. The resulting mixture was cooled to room temp. and concentrated under reduced pressure to yield crude 1-(chloromethyl)-1-(cyclohexylamino)cyclopentane HCl salt (2.84 g), which was used in the next step without firer purification.

Workup

temperatureThe resulting mixture was cooled to room temp.
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-2c95e3be24164d069c9b63100bdf0900
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Linked notes

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